Stop Being the Bottleneck: Keegan Sard on Delegation and Decision-Making

In this episode of the HabitStack Podcast, host Scott Ward interviews Keegan Sard, a fractional chief of staff based in Monaco who has been doing fractional work for 10 years. The conversation explores the critical difference between a chief of staff and a COO, and why chiefs of staff focus on the founder's priorities without P&L responsibility. They discuss why founders should hire fast and fire faster instead of endless interview rounds, and the distinction between executive assistants who manage calendars and chiefs of staff who make strategic decisions on the founder's behalf. Keegan explains decision playbooks for empowering teams without bottlenecking the founder, quick wins like eliminating payroll from the founder's plate and conducting calendar audits, and implementing the Ritz Carlton's $2,000 rule where every employee can spend money to fix problems without approval. They dive into why founders should include bad news in investor updates to get help before it's too late, the importance of listening tours in the first 90 days, and why anonymous feedback reveals customer insights that never make it up the chain.

Transcript

Scott Ward (00:02)
I'm Scott Ward, founder of HabitStack and I have the distinct pleasure today of hanging out with Keegan Sard. Keegan is a fractional chief of staff based in Monaco, originally from Australia. We're going to hear about how that happened. He's been doing the fractional thing for like 10 years, which is way before fractional was a thing. And so we're going to hear about that and some other things that he's been up to. So yeah, it's a real pleasure Keegan. Thanks for coming on the show with me.

Keegan Sard (00:27)
Really happy to be here. Thanks for having me.

Scott Ward (00:29)
Australia to Monaco. Tell us about that.

Keegan Sard (00:31)
Well, it was the middle of COVID. Australia decided to be a communist.

Scott Ward (00:34)
That's all I gotta say. That's all I gotta say about COVID.

Keegan Sard (00:37)
Yeah, Australia went

pretty hard during COVID and I disagreed with the public policy position. So I took a one way flight and I left and I've never been back since. So it's been six years now. ⁓ It's been a long time. So I spent some time in Dubai. Dubai is a great, country, the UAE, ⁓ but it wasn't for me. I really wanted to try Europe. So I said, you know, ⁓ if, Monaco works, I'll stay and if it doesn't, I'll go back to the Middle East. So yeah, they,

Scott Ward (00:48)
Wow.

Keegan Sard (01:03)
me. So I've been here now over five years and be six years in October and I'm a very happy man for the privilege of being able to call Monaco home. It's a beautiful place in the world.

Scott Ward (01:13)
I don't really know that much, I'm ashamed to say, about Monaco. What is it like? What's drawn you there? What's kept you there?

Keegan Sard (01:19)
It's a little village, but ⁓ everyone has a bigger yacht, they like to say. So there's a mixture of cultures. There's only 39,000 residents and about 8,000 citizens. And ⁓ it's run by municipality, so it's very small. It's two square kilometers. And it's got the best of everything. It's got the beautiful weather. It's got arguably one of the best governments in the world. Low taxing. The Prince is an absolute legend. And you see him.

Scott Ward (01:31)
Wow.

Keegan Sard (01:45)
Every day, you know doing different events and other are very approachable. You can say hello You know one of my favorite stories was he was in you know, a pretty pretty good dive bar that we like here in Monaco and He goes to get his own beer and there's these two American tourists and they go What's it like living in Monaco? Yeah, it's good. He goes. have you met the prince? He goes. Yeah, nice to meet you And that's that's the nation the notion of this place the this place

is about opportunity and it's such a pleasure to call it home. I bleed red and white, my friend.

Scott Ward (02:17)
Oh, that's cool. kind of made me want to visit someday. Maybe I'll knock on your door. So the other thing that there's some history there that I wanted to ask you about is Shark Tank and some kind of beer delivery, something, you know, like what's that all about? We'll talk about Chief of Staff and everything like that, but it'll help us get to know you a little bit better with some of the other things you've been up to. That sounded interesting. Tell us about it.

Keegan Sard (02:22)
Please do. ⁓

I'm

Sure, so I've been very entrepreneurial my entire life. Well, ⁓ previous life I started flying airplanes at 14. Thought that was my career and absolutely hated the sort of the rigid nature of flying. It's like you have to go here and you have to wait and then you have to come back. Like I don't like being told what to do so that didn't really last long. So got an opportunity to set up a little startup and we called it Friday Beers and we delivered a six pack of craft beer to your desk on a Friday afternoon and it was a lot of fun.

So we got in a lot of trouble with different buildings and we got very creative of how we smuggled in beer to people's desks because they weren't allowed to and yeah, we randomly saw a tweet by a guy called Steve Baxter who was one of the Australian sharks and he goes well when are you delivering us beer and we said Friday and we purposefully made him last so the whole day is tweeting us like where's my beer where's my beer and it went viral and then we said hey, you know, maybe we should apply to Shark Tank he goes well I have no say

Scott Ward (03:28)
⁓ yeah. ⁓

Keegan Sard (03:34)
in that. So put the application in and we got the call up and we were on channel 10 and it was a great experience. We got investment from Steve, which was even better. ⁓ unfortunately though, we aired on literally the Australian version of the Super Bowl. So we didn't have the uptick that we would have liked. And that's just luck of the draw. So we did it for a few years and then we parted ways and sold the list. ⁓

Scott Ward (03:44)
Yeah, yeah.

Keegan Sard (04:01)
So we made a little bit of money along the way, so we can't complain. And drank a lot of beer.

Scott Ward (04:05)
Yeah, well, and you know what? Today's Friday. So I could use a six pack in a little bit here. Not quite yet, but in a little bit.

delivery time would be a little bit long. Cool. Well, that's a fun little bit of context for you. Let's shift into what you're doing now. And how, 10 years ago, how did you get pulled into doing fractional work? The fractional part is interesting and also the chief of staff part is interesting. think, what is fractional versus other models? And also, what's the chief of staff?

Keegan Sard (04:35)
Well, actually what happened after worked in, after aviation, I did a property degree, I did project management work in government, did that for five years and then got an opportunity to work in technology consulting. So implementing consulting projects across big four.

mining, financial services companies around Asia. And that was a lot of fun, but in 2014 decided to go out on my own. So in 2014, you know, bit the bullet and set up my own shop. And I was pretty much on a daily rate. I wasn't fractional. I was like, I'd come and work for you for a couple of weeks and the next guy would call me and I'd fly there and do that. And, I did that very successfully until 2019. And then of course, 2020 COVID hit and I couldn't travel anymore.

Scott Ward (04:56)
me

Keegan Sard (05:21)
I couldn't, my modus operandi was why don't I go to where you are and take a daily rate, do a couple of weeks, fix your problem hopefully, and then fly home. But in 2020, couldn't do that, so I had to pivot. And that's when the whole idea about the Chief of Staff role came up. I took a full-time Chief of Staff role to start with, and then that finished and we parted ways. And I said, well, why don't I do this fractionally? It's better for me. If you are a fractional, ⁓

freelancer,

you get to pick your projects, you get to pick your audience. If you don't necessarily like the founder, you can pivot to a different founder without it hurting your bottom line. So it's been quite nice that way. I guess to answer your question, Fractional is all about, it's like part-time, but without a time, it's mainly project-based. So you're coming in to solve a problem and you might be there for a month, you might be there for six months, and you're rarely there for a year.

Scott Ward (06:01)
Right.

Is that kind of the way that you do fractional or is that do you think the most fractionals, people who call themselves fractional, that's how they see it? Like it's a short-term gig.

Keegan Sard (06:23)
I there's different views on this but

Scott Ward (06:27)
Yeah.

Keegan Sard (06:27)
Some still are in the hourly rat race and I don't believe in hourly billing. think that if you are good at providing value and you have a good impact at the end of the day, you should have a retainer and you shouldn't be a bank, you should be paid in advance. So that's how I see it and I have one client that I've stayed with but only because he's become a good friend and he doesn't want to change. He's sort of, you know, allergic to change. So I keep him on my books but everyone else is, you know, three to six month engagement.

move on to the next one.

Scott Ward (06:58)
So what kind of stuff? what are the signals that maybe there's a need for something, some help along the lines of what you do? And I guess it's just kind of like, what's your bread and butter in terms of ⁓ helping out?

Keegan Sard (07:10)
For me, it's early stage technology startups. So they're not at series A yet, but they have a little bit of money. The founder is very good at their niche, whatever that is. I like to say there was a guy that coined the term zone of genius. He's very good at something, but not good at everything. And now he's scaling and he's got money and he just doesn't have any processes, doesn't know how to manage people. And he needs someone to be his right hand. And I think that's a really good segue into what a chief of staff is.

So you're working with the founder to focus on their priorities, their projects, and give them more time back in their day to focus on what they're doing really, really well.

Scott Ward (07:39)
Right.

Yeah. So like one question I have is what's the difference between a chief of staff and a COO?

Keegan Sard (07:53)
Well.

A Chief of Staff comes in earlier, think, to certainly an early stage technology company. And your priorities are the founders. You're not the entire business. I have a controversial take that if your founder leaves the business or the CEO leaves the business, you should leave too. I think you should be loyal to that person, not loyal to the business. And the big difference is you don't have P &L control and you don't run day-to-day operations. ⁓

Scott Ward (08:20)
Mmm.

Keegan Sard (08:21)
CEO also owns departments, right? They have a high level view of ops, finance, legal, and even sometimes sales, where I might come into the sales team and fix it, but then I leave it, and then I go to the next problem.

Scott Ward (08:32)
You don't have

to report, you don't take on direct reports or anything like that.

Keegan Sard (08:35)
Sometimes it does happen, but it's not normal. And we certainly don't have P &L responsibility, right? And that's where the COO comes in.

Scott Ward (08:43)
So I could imagine, well, let me ask you one thing. So I think you probably, you probably take the position that founders and CEOs should get help. I'm guessing. And a lot of times where they really think of first is like an executive assistant. I need somebody to do management calendar, my emails and keep me organized and that kind of stuff.

Keegan Sard (08:53)
Yes.

Scott Ward (09:05)
And I think that there's a lot of situations where that's a good idea. That's not a bad idea, right? so help listeners understand kind of like the differences, but also when to leverage which role.

Keegan Sard (09:19)
An assistant is a crucial part to any founder's journey or any CEO's journey. They are the gatekeeper. They need to make sure that emails are taken care of.

calendar managements are certainly a big key point to that, ⁓ travel, et cetera, but they are not a chief of staff. the roles are so different. And we see a lot of times that they try to merge both roles. And a good chief of staff is at the intersection of strategy and has decision-making authority. I always give the example that you can go to the meeting on the left and I can attend the meeting for you on the right. And I can make the decision in that room.

there. Now an EA can't do that. It's not a position for promotion in 99 % of cases and I'm very vocal about that on LinkedIn.

Scott Ward (10:05)
⁓ yeah. So, okay. As you're, I would have guessed based on what you described me, I guess there are the times where as the, as the chief of staff coming in, you're finding areas of, they need improvement and, and, solving them. And one of them is, dude, you should get an assistant, you know, I'll help you find an assistant, right? That's part of what you, one of the systems you put in place or roles that you put in place.

Keegan Sard (10:20)
Yeah, great.

Scott Ward (10:27)
Do you think the founders are too quick or too slow to pull the trigger on hiring an assistant?

Keegan Sard (10:32)
I think we've, since COVID got into a habit of being too slow to hire, full stop. Yeah, it's, how do I explain it? Seven rounds of interviews is too many for any role.

Scott Ward (10:38)
Mm. Or just generally.

Keegan Sard (10:44)
And I've seen guys at not only corporate level but start-up level literally have to meet everyone, do take-home exams, all the rest of it. Bite the bullet, hire the person, bring them in as a contractor. Especially with the US, you've got the 1099 contractor rules, right? Bring them in as a contractor, test the waters, see if they're a good fit, exit them within 90 days. Why is it taking up to three months to hire someone? Blows my mind. It limits growth. Most of the time, and I say this,

generally speaking, if you're coming in front of me, you can already do the job because of what you've shown me in your CV and who you used to work for. So it's now about cultural fit and do I like you and can I have a beer with you? And then are you gonna get along with the team or are you gonna be the polar opposite? That's really what we...

Scott Ward (11:26)
Just pretty tough

to discern, but pretty tough to discern from interviews anyway.

Keegan Sard (11:30)
Of course, my favorite is we want to talk to a reference. Who in your right mind is going to give you a bad reference? Never. Unless they don't realize the guy is going to give you a bad reference and you've given the wrong name.

Scott Ward (11:37)
Yeah.

Yeah. Yeah. Although, you know, I think it doesn't, so it's not a, it can, it can weed out. It can weed out some people actually, because, if the, you know, the reference actually doesn't exist for like, you know, that kind of stuff. So it's worth calling anyway, but, but, ⁓ yeah, but how do you manage that though? Can you, because like the, ⁓

Keegan Sard (11:52)
Yeah, sure.

Scott Ward (12:00)
Yeah, it's fine to hire fast and fire fast, but also people are leaving their jobs. They're leaving their other job to come on board. I think maybe, don't you think that's the reason why people are, part of it, why people are cautious and slow?

Keegan Sard (12:12)
I like to work with people that make decisions fast.

know, most interviews are much longer, you know, you're talking weeks and then they go, ⁓ look, we've decided to hire internally. And I think there's nothing more disgusting in the current environment is wasting someone's time with multiple rounds of interviews and prep. Because it's not just the hour I spend with you, Scott, it's the prep to meet with you and then your COO, CFO, et cetera. It's horrible.

Scott Ward (12:34)
Mm-hmm.

Yeah, I agree. I think that as much as possible to get some experience working together, just, mean, it's astronomically more signal that you get from that when you can do that.

Keegan Sard (12:49)
And most of the time you might have the dream candidate. It might look fantastic on paper and they come in and they're horrible and you fire them anyway. So I just always say, know, hire fast, fire faster.

Scott Ward (13:01)
Do you, are you seeing, so people are hiring slow, slower than you think they should. Are they firing fast or are they also firing slow?

Keegan Sard (13:10)
bit of both. I don't think it's consistent, but I am seeing consistency on the hiring. I think, you know, with the rise of AI, we're seeing mass layoffs, you know, we've had, you know, over 100,000 mass layoffs in the corporate sphere just this year already. And it's going to be much worse by the end of the year.

Scott Ward (13:10)
Yeah.

Keegan Sard (13:29)
I would rather give someone a chance to exceed, to excel and then, to exceed expectations rather than, you know, waste their time over six, nine, 12 weeks. And they're off. At least they had a, at least they had a check for 12 weeks, you know, like, Hey, bring them in. Let's go.

Scott Ward (13:44)
Yeah. Okay. So when, when, when you're working with the founder, what are some things that you see early on? It's kind of like classic, typical things like, man, yeah, that should come off your plate.

Keegan Sard (13:55)
that's easy. So.

When I come in at that seed stage, the founder's still doing payroll. And I'm like, why you, what's on Friday? They're like, oh, I gotta pay all the staff every two weeks. I'm like, okay, but why is it taking four hours? Oh, well, everyone wants to get paid differently. And I'm like, why aren't you using a tool like Deal or Gusto for that? That doesn't make any sense to me at all. So that's an easy quick win. And the other one's a calendar audit. Just looking at the last four weeks of your calendar and saying, what's founder only? What's a really critical decision?

Scott Ward (14:00)
Right.

Keegan Sard (14:24)
that you need to be there for and should stay on your calendar. What can we delegate off your calendar? And what frankly can we delete? Because we just, it's crazy to me. And the other big ones are status meetings can be an email. Yeah, okay, we can do an all hands once a month or whatever, but like all these meetings, know, what was it? Spotify did it really, really well where they calculated the cost of meetings. So when you booked a meeting on your calendar, it said how much the cost was with all the people involved.

and straight away they started to reduce meetings. think Elon puts it well, if the meeting starts and there's no value added for you, walk out.

And he gets it. And the other one is like vendor or admin calls. And the big one for founders early stage is document prep. That's something that you can delegate to me is achieve this stuff tomorrow. So investor relations briefs, decks, know, partner presentations, all the rest of it, you should be providing input. Sure, but you shouldn't be building the debt. There's a thing that just come to mind now.

Scott Ward (15:21)
Right.

Yeah, yeah, yeah, that's a list. What are some of the things that, okay, strategies for balancing these two realities? One is founders need to be free to do what they do best. A lot of times that's around growth. And also, you know, staff need to be empowered to make decisions and to have enough autonomy to move forward on things.

But also, people do need input from the founder. And so you can kind of fall off the wagon or fall into the ditch on either side. What are some strategies that you see working for founders to be able to provide the relative, sometimes it's five minutes. It doesn't take a lot of input, but then the person's waiting for two weeks to get that five minute input. It's really frustrating for the staff.

Keegan Sard (16:02)
Now, again.

Scott Ward (16:06)
How do you kind of manage the two priorities there?

Keegan Sard (16:10)
waiting two weeks is 4 % of the year, right? That's why you have a Chief of Staff. Because they can prioritize the decisions, they can prepare decisions, and sometimes if you have a really good relationship with your founder, they can make decisions on the founder's behalf, but they can keep leadership aligned, and I think that's really critical. Your leadership shouldn't be necessarily bothering the founder every single five minutes, especially at pre-Series A levels. Go to the Chief of Staff and say, hey, I haven't heard from Scott today,

Scott Ward (16:13)
Yeah, yeah.

Keegan Sard (16:37)
what I need, it's been a week, where can we move this forward? And a good Chief of Staff will either be right, I know the answer, or I'll get you the answer and I'll get it to you literally by tomorrow.

Scott Ward (16:48)
Right. Yeah. Yeah. I think that's so, so, okay. What you're saying there is you kind of the chief of staff can serve as that conduit to make sure ⁓ that the, doesn't go too long, especially if it's an easy answer. What about for people who don't have a chief of staff? Like what, ⁓ structures and I'll tell you one thing that I, that, I think is an interesting idea that I just talking to somebody about his office hours. So basically, you know what? I'm not going to field,

Slack messages and, and, and like, do you have a second kind of inquiries just ad hoc throughout the day? I'm going to have office hours once, maybe even twice, but for short times per day. And so it's just like defer your question. Everybody come in and I'll just boom, boom, boom, boom, boom, rattle through them as fast as we can. And, you know, that would kind of batch the batch, the input in a lot of times. mean, frankly, sometimes what happens is that.

Well, if I gotta wait two hours till office hours, I guess I'll just do it. And that's a good outcome or I'll just figure it out myself. That's a good outcome. But it doesn't leave people hanging for so long. There is a consistent way to get the input that they need. That's not, you know, it doesn't take so long. I don't, any hot takes on that approach?

Keegan Sard (17:56)
I love office hours, I think it's great if the founder is consistently coming. know what I've seen in the past is office hours are the first to get cut from the calendar next week.

Scott Ward (18:01)
Right.

Keegan Sard (18:05)
Cause it's beautiful in theory, but then it's like, I've got an hour block. I'm just going to get rid of that. And I'm going to go back to what I was doing. Right. the big one is a decision playbook. I would say to any founder that doesn't have a chief of staff is do a decision playbook today give clear ownership to different parts of your strategic vision So you go right. And the initiatives in that vision and say right Scott you own it You will make the call Yes you'll have contributors that will give input but you will make the calls and then you will inform us

later And that is key when you don't have someone in that spot

Scott Ward (18:37)
Yeah,

that sounds interesting. Can you unpack that a little bit more? what's an example of a decision playbook in a certain area that kind of I'm imagining it has the various constraints. In other words, you can't you can't decide to spend a million bucks, but you can decide to spend a thousand bucks or eight or whatever or 10,000.

Keegan Sard (18:50)
Nope.

I'll give you

two examples in sales, right? So my last sales team that we built from the ground up, I said, right, you're paying the guys 180 base. You're paying the head of sales to 20 or 230, I think it was right. And I'm like, it's an enterprise deal. So it's going to take up to 12 months to close that. You need to, we need to feed the guys in order for them to live for the 12 month sales cycle. That's number one, everyone forgets the sales cycle. Number two is, okay, you're paying them that 180 base,

Scott Ward (18:56)
Yeah.

Keegan Sard (19:22)
What support are you giving them? Yes, there's the CRM and the tech stack and all the rest of it But do they have a travel budget? Do they need a travel budget? Is there a conference budget and You put a number to it and you don't worry about the weeds you say to your head of sales Your conference budget is 30k spend it how you want your your travel budget

Scott Ward (19:41)
But spend it.

Don't spend it.

Keegan Sard (19:43)
Yeah,

spend it, go, I don't care. Just like expenses. You know, I wrote a very popular LinkedIn post about this. I love to pay my reps 15k more a year in base. So they never given me an expense claim for a coffee or dinner or drinks. There's nothing worse than you take a client out and you know that the budget in the playbook is 300 bucks per dinner and you're already at 400 but you know Scott's gonna spend money, right? So you're like, well, do I

I go outside and call Keegan at like three in the morning and say, hey, I'm gonna spend more or do I just get the cut on the wrist tomorrow morning? How about I just pay you more and you either pocket it because you're gonna hit your KPIs anyway or you've got freedom to spend. Easy. And it all comes back to that decision playbook. I'm not saying you spend a million but there's got to be, you've got to trust your team to get the deliverables that you want. If you want to build a billion dollar business, you need to start spending money.

Scott Ward (20:38)
Yeah, and I think it's not just about spending money also. It's kind of like, you know, if you, so if you want to, anybody, or I don't know, you can do a LinkedIn post without it being reviewed, but you can't do a, I don't know, white paper or something. I like this, I think you're right. Like there's a lot of pretty easy to discern lines that just make it so that ⁓ things can move. It's painful. It's painful when it's like everything has to be reviewed too tightly.

Keegan Sard (21:00)
Yeah.

If I'm hiring a head of sales, head of marketing, head of customer service, I want them to actually be empowered to make decisions. The best one in the world has to be the Ritz Carlton. In the Ritz Carlton, every staff member can spend $2,000 to fix a problem without management approval. So that's the cleaner all the way to the general manager.

You have 2000 without any authorization. And the best example of that that I saw was a guy who went to the Ritz Carlton as a senior manager or a VP, came back, was running a different hotel brand in Australia and implemented the same policy. His valet called him or concierge called him and said, ⁓ I won't be in in two days time. And the guy goes, well, you're going to be sick in two days time. And he goes, no, Mr. Smith has locked, lost his passport. left it in a safe.

Scott Ward (21:38)
Right.

Keegan Sard (21:50)
and we were having a conversation. I know he's flying out of Perth tomorrow and there's a flight in 45 minutes so I got the manager on duty to use the corporate card to book me a flight so I'm gonna hand deliver him his passport. And it was under the 2K budget, right? Now what did Mr. Smith do? Well, he got to London for his business meeting. He didn't miss it. And where's he now gonna spend all of his money and tell everyone about that positive experience?

Scott Ward (22:13)
Of course, yeah.

Keegan Sard (22:14)
So like decision playbooks make sense at any stage of your business but if you're making someone the head of a department empower them trust them And if you can't trust them get rid of them

Scott Ward (22:25)
Yeah, that's powerful.

Let's talk a little bit about KPIs. I'm guessing, I'm guessing that one of the things that you help folks do is to start running, instrument the business a little bit, right? So we can run this thing with some, via the instruments and not have to do it by feel because it's hard to scale that. Is that true? And what's that process look like?

Keegan Sard (22:38)
Exactly.

Most startups at early stage have no processes at all, no KPIs. All their KPIs just like, we need MRR to go up in tech sales. It's just MR and ARR. And you're like, okay, but what about everything else? Yeah, nah. What's your ROAS? They're like, I have no idea. How much are you spending on ads? Oh, a hundred grand a month. Shit, okay, let's have a look at that a bit deeper.

Scott Ward (22:57)
Yeah, yeah, that's right.

Yeah. Yeah. Yeah. Yeah. What's the like the quick and dirty, like just in really concrete terms, like what do you actually set up for people? Is it just the spreadsheet by the week, some kind of thing, or like what's the quick and the actual concrete detail there?

Keegan Sard (23:22)
Well, I think every department's gotta be using a tool, right? So for example, sales should have a CRM and the data should be in there. And then usually you find that the sales reps are really lazy because they've not been taught to play with data properly, right? So you just make one change. You go, hey, you want your commission? It's gotta be in a CRM. No, not in a CRM, no commission. Changes pretty quickly.

Scott Ward (23:44)
Yeah,

yeah.

Keegan Sard (23:45)
With spreadsheets, it's very easy, but now with AI, can create spreadsheets. Cloud Code is changing the game here. We can create dashboard views very, very quickly. And I think that's, it's just keeping people accountable. That's it.

Scott Ward (23:58)
Yeah. Do you recommend that leadership teams have like a weekly or monthly KPI review meeting of some sort? Or what does that look like?

Keegan Sard (24:07)
I think it's always good. Well, I like investor updates. I'm very big on this. You your key metrics for whatever business you're in. If you're software, it's like MRR ARR growth rate.

I would put in your key sales metrics. you chuck your sales team in there, name them in that investor update or that brief, and then say, right, okay, Scott's our highest performer. He's brought in X amount of dollars. John's lagging behind, but very close, et cetera. And then one thing we always forget to do with our investors is we always tell them the good news, but I think we need to tell them the bad news. And then also say, there's always that line, what can I do to help? And it's like, ⁓ I need an introduction

Scott Ward (24:40)
Bye.

Keegan Sard (24:46)
senior engineer because that's our biggest issue right now or we're burning too much capital, we don't know where we need someone financial to come in and have a look. Maybe you know a CFO fractionally that can come in and have a look, right? I think we fail to do that and leadership can do that very, very easily. Again, leveraging AI, you can pull all that data from all the different systems and chuck it into a weekly report that just literally goes to the leadership channel in Slack and then you can have a conversation about

I don't think you need an extra meeting. I just think you need the data in front of you to make better data back decisions.

Scott Ward (25:17)
Yeah, so I mean, that's kind of an interesting thing that you said earlier, where like you should include the bad news. think there's a certain, well that makes sense just in terms of kind of integrity, honesty. But I think what I'm guessing that you have in your experience, there's kind of like some utility to it as well. It's not just about honesty, which is also important, but what is it that you see leadership teams and founders?

getting when they are frank about what's going wrong with their investors.

Keegan Sard (25:47)
Look, it depends on your relationship with investors, but from when I've briefed investors, they want to know before it's too late. No one wants to know you're out of money tomorrow. They want to know you're out of money in three months time.

You know, the great example I have is when Brad Godfrey created Virgin Australia. He went to Richard Branson in the UK and said, hey, I want to create a new airline in Australia. And they did a back of the envelope sort of numbers session. the next day, Brett's accountant in Australia called him and said, hey, why is there 10 million in your bank account? And he goes, let me call Richard. Richard goes, green light. And he worked up to, I think it was

Scott Ward (26:20)
Yeah.

Keegan Sard (26:22)
12 or 13 months in the business and the CFO walked into the company and said, Brett, it's been a good run, but we're out of money. Eight million just wasn't enough. Brett goes, lucky you've been holding back too from me. And that's the whole point, right? He knew that if he put the 10 million in, they would have found a way to spend it. But.

you know, being creative, he knew that if he just held some back in the high interest savings account, it was the time where they needed it and straight in. And the company's now listed and it's gone through a few hands, but I think external factors have been the biggest issue to that. But ⁓ that's a really good example of how it can be done properly.

Scott Ward (26:46)
Right.

Mm-hmm.

You know, one experience that I notice founders regularly have is the feel like

things used to move a lot faster It was fun We would have ideas and action them really quickly And now it takes so long to get anything done And I think there are some times where they're right that things are too slow now and something needs to be fixed. And there's other times where well we're in a different mode now how do you tell which situation you're in?

Is it true that something's broken or is it just, you know, this is just a larger company and it just takes a little more time to do things?

Keegan Sard (27:38)
I think my biggest issue is when someone makes the decision to change they used to give it more time. We've all put in a strategy into a different business and it's starting to work but maybe not work as well or as quickly as we wanted

what I found in doing this for now over 10 years is that they will pivot too early to actually seeing it through And I would rather be entirely wrong than leave a little bit of time on the table So I like to say when I'm right I'm happy When I'm wrong I'm grateful it's give the strategy a bit more time because you only need a mistake to happen or that gift from God and it just puts you on the right path And we've had that at various

startups, worked in the EdTech startup. It was a language miscommunication with what the client thought I was saying versus what I was saying that we did 2.2 million in sales in 12 months. Now, that was, it was genius. Like, but if I walked in and said, oh, we're going to make this change and it's going to work. Of course we would never have done it, but it was just pure luck. And I think sometimes founders just need a little bit of luck too

Scott Ward (28:43)
and need to put themselves in the way of luck, but then give it enough time to let the luck strike. But of course there's some times when you hang on too long. I'm asking these impossible questions because many things are only definitive in retrospect, but any signals that you look for to say, no, no, no, like, you know what it is, we've played it out enough. It is pivot time. This strategy didn't work.

What do you look for there?

Keegan Sard (29:10)
Well, I think you've got to listen to your persona or your target audience. If your target audience isn't biting, they might be biting slowly, you know, it's fine. But again, it comes down to your sales cycle. You know back from data if it's going to work or not. So if your sales cycle is 12 months and now it's 10, great, perfect. But if you're complaining at seven months, give it some more time. The data previously has been that it's a 10 to 12 month sales cycle.

Scott Ward (29:31)
Mm.

Keegan Sard (29:35)
I think that's where we've dropped the ball a little bit.

Scott Ward (29:38)
Cool. Okay, so here's a question for you. I'm a ⁓ goal and accountability guy, and so I can't help myself. I wanna see if we can make some things concrete in terms of what would a goal look like? I guess the question is, well, let's start here. What are some major projects? So things that are like multi-quarter things that it's gonna require in terms of time for you to help a company put in place. What are some of those examples? And then when we get those...

Let's craft a yearly goal that would represent success. Start with the projects first. What are some examples there?

Keegan Sard (30:11)
of as a fractional chief of staff, right? Yeah, so like coming in and say the founder has a really good strategic initiative that they want to bring into the business, but no time. So now I can wear that hat, I can go off and try and solve that problem, bring that into the business. It could be, hey, we want to release this new feature, but we don't have a project manager to run that new feature. So working.

Scott Ward (30:14)
Yeah, yeah, exactly.

Mmm.

Right, right. Or we're

going to go up market. We're going to go up market, you know? And so that means a whole bunch of things. We got to have better support, different support. We got to have more compliance things. It's like a very big opportunity, but it's going to, there's a lot of moving parts. Okay. That's a good example.

Keegan Sard (30:48)
So that's one that happens all the time. Or I come in and I say, guys, the sales team is a disaster. You're not giving them enough resources, enough money, or unfortunately, maybe they're just not a good fit. So it could be come in and fix, come in and replace, or come in and build, right? Sure.

Scott Ward (30:51)
Yeah.

Yeah. Okay, good. Let's take that one. Let's take that one, Keegan.

12 months, I know sometimes you're not there for 12 months. We'll say you are. So look, 12 months, what's going to be true? How do we articulate the measures of success at the end of those 12 months with regards to fixing sales? I mean, it's revenue. It's always sales. Sales is actually the easiest one to measure. But what else? Let's say a couple of other kind of KPIs or measurables that you would add in there.

Keegan Sard (31:23)
Exactly, it's perfect.

Well, I'll give you another pivot is people. know, founders are not good people leaders. You know, they don't have sometimes the EQ required to understand people. You notice that by glass door recommendations being really bad or the sentiment in the office not being good, right? You don't want all these negative reviews on glass door that it's a terrible place to work, etc. Right. So again, a good chief of staff can come in, understand the problem,

Scott Ward (31:41)
right.

Keegan Sard (31:54)
at the people level and it's not just money. It could be flexibility. It could be stress and being overworked, right? know, startups have a really big failure rate in the fact that they believe, some founders believe, I will say this, some founders believe that you should work as hard as them. And that is simply not true because you were not incentivized to do so. Now, if you were incentivized to do so, happy days. But you don't have the equity.

You're not as passionate. You're impassioned about the outcome but not as passionate as the founder because that was your life's mission, right? So founders make that mistake every day of the week. Why aren't they working as hard as me? Well, you've given them 1 % equity on a four-year vest. Like, what the fuck? It doesn't work.

Scott Ward (32:36)
Yeah, yeah, I think I've seen that as well. There's a, it can be very frustrating, you know, like I feel lonely almost, right? Like I'm, basically care the most about this business. ⁓ although, they're also quick to say, like, I mean, my people are great and they do really care. ⁓ sometimes I wish they would care even more, you know, but here's the, okay, let's take that one. That's a, that's a good one. So, ⁓ the, your, your, ⁓ so the, the yearly goal is something like, fix the culture or.

Keegan Sard (33:03)
Yeah.

Scott Ward (33:04)
Fix morale. know, make it so people are getting along and we're all having a good time instead of a bad time. You know, so how would you measure that? How would you measure success at the end of the year?

Keegan Sard (33:13)
How many stuff are you losing at the end of the year?

Scott Ward (33:15)
Yeah, sure. Yeah, exactly. Retention

rate.

Keegan Sard (33:18)
Can you hire? I've got one startup that I'm working with right now, aggressively hiring. I think they've made 17 new hires this quarter. That's huge. How do you make sure that they're onboarded properly? They feel like they've got everything they need to perform. They're very much remote first, so that's even harder because you don't see them every day. It's okay for people like you and me, Scott, that are very extroverted and we sort of put our hand up and say, hey, what's going on here? But the introvert doesn't say anything.

Scott Ward (33:37)
Yeah.

Keegan Sard (33:46)
The Asian culture for example is saying nothing and complaining to everyone else. That's just how it works. And then you're like, I didn't know he was unhappy. He always seemed happy. So I think it comes down to churn and high ability and can I feel this? Because if you have these glass drawer reviews that are horrible, I'm telling you, people aren't gonna say yes.

I even had one founder, it was hilarious. She said to me, you want to pay this guy more than I get paid. I said, hang on a minute. You have equity. You have 60 % of the company. What are you on about?

Oh yeah, but it's just the, what's it called? The optics of it. know, like, oh, but the optics, know, when I do payroll, I'm like, well, one, you shouldn't be doing payroll anymore. And two, it doesn't matter because that person is going to increase your business three or 10X, you know, done, move on.

Scott Ward (34:30)
Yeah.

Do you, so I think regrettable churn is a good one. Non-regrettable churn is maybe a good one either, won't that to be, that could be healthy. But here's engagement surveys, that kind of stuff. Do you see any value in that kind of thing? Yeah.

Keegan Sard (34:44)
Yep. Yeah, I think we it all the time.

I think we don't there's two things we don't do we don't tell we don't ask the staff their direct responses about how they perceive the business and I mean at all at all levels. I don't want just the leadership's view of the world. I want the juniors view of the world. Maybe they've got a great idea.

You know, when I, when I worked in property development, right, we had, we, used to run this table of a dinner once a quarter and I had engineers, architects, and I had the juniors there and this junior engineer goes, ⁓ he had a few too many to drink, right? He goes, yeah, but the building's going to fall over. And he's, and I'm like, sorry, what? And then the senior engineer got all pissy and upset, right? I'm like, no, no, this is Vegas. What happens in Vegas days in Vegas speak.

right. The kid was right. There was a big error in one of the drawings that could have mean not not a catastrophic failure of the building, but certainly a problem down the line of movement or whatever. And we found it because we let the small guys speak up. The cleaner in the some of the best organizations, the cleaner knows everything. gets treated the worst and knows everything about the business because they're there overhearing things every single night when no one else is there.

Scott Ward (35:55)
Yeah. I mean, how make it some takeaways, give some takeaways for a, for a founder, you know, maybe they got 30 employees or something like that. And engagement surveys is there a, complicated does it need to be? Where do they get this? How often do they send it? What do they learn from it? You know, just what,

Keegan Sard (36:05)
We're just testing.

It's literally be

a suggestions box that's just anonymous and no holds barred, right? Like you're not going to criticize someone for saying something. That's an easy win. What we don't do is ask our customers enough information.

I love what Sean Ellis and Ray Olvera did at Superhuman. They did the product market fit survey. So that's brilliant. If the product wasn't here tomorrow, would you be very disappointed, somewhat disappointed, or not disappointed at all? And then that guides roadmap. That's great. Keep the guys, 50 % of your time is keeping the guys that are very disappointed, and 50 % of the time is trying to get the very disappointed to go up or stay the same and not leave the product. Because if they're not disappointed at all, they're going to churn out.

Scott Ward (36:31)
Right, right.

Yeah, have you seen some, what's an example of somebody who's gotten kind of like anonymous feedback around culture and like, ⁓ man, actually that's right. And then they were able to fix it. it, does anything come to mind?

Keegan Sard (37:05)
It

happens more than you think. And it usually is around the fact that they're not listening to customers. So you'll find that the CS team that's doing a lot more work with customers at the junior level, because they're on the phones, or they're doing the emails, or they're doing the support tickets, are seeing a narrative that you're not picking up.

Scott Ward (37:22)
I see. they're saying like, look, customers are kind of ticked about this and you do not. then it comes out because they're not talking to customers. It's coming through the channel of of support.

Keegan Sard (37:31)
great example would be I believe commissions for sales teams should be the same if it's a renewal or a new business. Because you have way more to lose and so much out of your control as a sales rep when you are a client versus when you're not. But everyone goes, no, renewals are easy. No they're not. What if the CS team makes a mistake? What if there's a feature missing? I know in EdTech we lost a huge deal back in the day. It was like an $85,000 contract because we didn't have SSO.

And we say engineering SSO SSO. no, it's I'm like pay fucking 15 people like let's go. Let's just build it. know, it's if we had that, you know, coming up the ranks from other people complaining about it, maybe it could have got put in earlier or been on the roadmap earlier to ensure that that renew.

Scott Ward (37:57)
Hmm.

Yeah, yeah, cool. That's good advice. One thing, before I let you go, I wanted to ask you about, you talked about doing, and I think this is maybe, if you were to take this people goal and chunk it down to the first 90 days, you said something in our prior conversation about a ⁓ listening tour. Say more about what that is and what kind of questions you ask people.

Keegan Sard (38:32)
Yep.

I think

this is why when I'm a fractional chief of staff, I love working on a three month retainer because month one should be about listening to the business. Yes, of course, finding quick wins and being able to implement them quickly, but you should be able to talk to everyone in the business and understand not only the founders problems, but what other people are experiencing with, again, no issues if they tell you something negative, right? It's not a blame game exercise. It's like how to self-improve because we can also

Scott Ward (39:02)
Yeah.

Keegan Sard (39:04)
I have zero patience for example. I try, I'm working on it. It's God's plan for 2026. Keegan, please bite your tongue a little bit more and be more patient. But I'm so passionate about the outcome and I want to see delivery work. It upsets me when another area of the business is letting the team down.

So listen to all the direct reports, then go a step deeper. Take the juniors out for coffee, you know, like maybe they've got a gem that you just didn't understand or maybe they haven't even highlighted it because they didn't even think it's a bigger issue, but because you've got a lot more experience, you can actually put that to work.

Scott Ward (39:39)
Yeah, that's a real, that's a real gift, right? Because I think as a founder, that makes a lot of sense, but man, it's hard to imagine spending, you know, going to coffee with everybody in terms of the time. it just, just to be. Yeah.

Keegan Sard (39:51)
Yeah, but we all have more time. Nothing upsets

me more than founders that make out their busy. No one is too busy to meet with you. Even the president of the United States can meet with you for 15 minutes, right? Like you're not that busy. Some of the biggest guys I know, and I've been around billionaires because I live in Monaco, right? Like the more money they have, the quicker they are at responding.

unbelievable. You send a text message, you know, I know of a guy who got a text message about doing a real estate deal for 130 million via text. Yes, proceed. Like no one's too busy not to reply. It kills me. It's like, I want to come over and strangle you because like no one's that self important, right? Everyone has five minutes.

You know, what I loved about Silicon Valley culture when I was living in Los Angeles was the fact that we would have meetings at 11.30 PM.

Because the guy in the valley goes, I've got no time. said, well, I'm up at 1130. He goes, me too. Let's meet at the diner. Done. And we would have the meeting, get it done. I love that saying, if he wanted to, he would. And it's so true. If you want to meet with me, you'll find the time. Weekend, public holiday, 2 in the morning. I don't care. Set the time. In person, remote, doesn't matter. My phone is always on.

Scott Ward (40:46)
Right.

Yeah, Keegan, can see how, well, I love the intensity, right? I love the pace. I can see how, you you would do a good job of injecting some hunger and some hustle into a situation. So I'm sure that you serve your clients well. It's been really fun to talk to you about these things, Keegan. mean, there's some takeaways that listeners can use right away and...

I've enjoyed hearing about, I'm to know more about what a chief of staff does and how it works in a fractional context and about Friday beers. It's been a good chat. I appreciate you taking the time to talk to me today.

Keegan Sard (41:35)
There we go.

Thanks for your time, Scott. Really appreciate it.

Scott Ward (41:40)
Adios.