Strategic Planning Is Broken — Here's What to Do Instead with Lia Izenberg

What if the strategic plan everyone's been waiting on is the very thing keeping your organization stuck? In this episode of The Ground Floor podcast, Christina Greenberg sits down with Lia Izenberg — executive coach, former nonprofit leader, and writer of the Leadership Material newsletter — for an honest conversation about why traditional strategic planning so often fails the leaders it's supposed to serve, and what to build in its place.

Christina and Lia unpack the difference between strategic planning (eight months, hundreds of stakeholders, a 30-page document on a shelf) and strategic clarity (a tight, leader-driven set of choices the whole team can actually rally around). They get into why the wide-funnel input process can leave staff feeling disenfranchised, where boards belong in the conversation, and how the absence of a real plan shows up in the search room — including how it shapes who you should hire and how long a new leader needs in seat before driving their own strategy work.

What you'll hear:

• Why "we did a plan, it's around here somewhere" is a leadership red flag
• How to tell the difference between gathering input and abdicating decision-making
• The questions that produce strategic clarity in weeks, not quarters
• What boards owe their leaders on goals, evaluation, and on-track conversations
• Lia's checklist for whether you actually have strategic clarity — or just think you do

If you've ever finished a strategic planning process and wondered why nothing changed, this one's for you.

Connect with Lia: liaizenberg.com | LinkedIn | Leadership Material on Substack 

Connect with Christina: edgilitysearch.com | LinkedIn | Forbes Business Council

Enjoyed this episode? Subscribe to The Ground Floor wherever you listen to podcasts. Leave a rating and review on Apple Podcasts — it helps more nonprofit leaders find the show. Follow Christina on LinkedIn for more on leadership, hiring, and building stronger organizations.

Transcript

SPEAKER_01 0:02

Hi. Um, today I'm sitting down with Leah Eisenberg, who is an expert coach, nonprofit executive, and educator. The theme of our conversation is that strategic planning is broken. And I think we're not saying that to mean the entire strategic planning always is broken, but that the way we often think about it is broken. So tell me, what do you think is broken about strategic planning today?

SPEAKER_00 0:24

I mean, I think what I've noticed is that there's a dissonance between what leaders actually need and what they're being asked to do, and that the industry, the folks supporting the strategic planning haven't necessarily caught up to what leaders actually need. And I think that comes from there's a lot of expectations. Board members want this and funders want this, and different people want different things when it comes to what's actually going to drive results and drive better leadership and cohesion in the organization. There's a difference between that and what we think of as a traditional strategic plan, I think. And we just haven't caught up yet in the language.

SPEAKER_01 0:58

Yeah, I think that's really true. And even if I think about from the search world, you know, one of the things we do when we first go into an organization is we always ask, do you have a strategic framework? Do you have a plan? And to be perfectly honest, when I ask board members that, eight times out of 10, it's crickets. Like they have a plan or they don't know what the plan is. And it definitely doesn't guide decisions.

SPEAKER_00 1:20

One of the first questions people will come in presenting with a lot of symptoms. A lot of times one of the root causes is lack of clarity on like what we're trying to do together and what that means about how we need to be together. And we're not coherent around a shared goal. And so people work in silos or people seem like they're focused on things that don't match what we're supposed to be focused on, or culturally, we just aren't aligned on values or what it means to work towards a specific goal. And so then when I'll sort of test, like, is there a clear strategy? And somebody will say, like, well, we did a plan, you know, it's over here, or you know, maybe not, or I haven't done it in a long time. And so, like, it's often the same answers as what you're describing from the board share. I'm coming from the leader themselves, or like they know, but nobody else knows what's in their head.

SPEAKER_01 2:08

And that's or it's really detailed plan that sits on the shelf, right? But it's very often that's I one thing you mentioned to me that really struck me was that a lot of the leaders you talk to too, they might have that overall plan, but they're struggling with okay, what does that mean for my actions every day, for my team, for like annual quarterly goals?

SPEAKER_00 2:29

Yes, absolutely. And then there's an alignment with fundraising too, because I think and the board and getting everybody on the same page and rallied around something, a strategic plan just doesn't inherently accomplish that. And so there's many reasons why strategic plans and strategic clarity, I should say, are required and necessary from rallying not just your team and yourself, but also your supporters and investors. So, what are alternatives? What I've been experimenting with lately is what's the difference between strategic planning and strategic clarity? I think strategic planning traditionally is a really long process. It could be eight months or, you know, a year or even longer. It can involve hundreds of stakeholders, it can involve complex landscape analyses and all these differing opinions. And you end up with, you know, a document with like, I've seen 30-page documents with 45 goals for teams of like eight that are just really complex and sit on a shelf. And by the time it's done, content's kind of shifted. Um, and so things are actually looking different. Folks are not invested, the message has gotten lost. And a lot of times, even like the leader themselves, what they care about and what they believe has gotten muddied. And there's an emphasis on more, more, more instead of less, us, less. Like strategy done well is like actually pared really far down. Um, and so what I've been working on with my my clients has been something just like strategic clarity as opposed to strategic planning. It's a lot of the same questions, but it's done in a sort of pared down intensive way. We're coming up with, you know, what's the vision? Where, where have we been? Where are we headed? What do we think it's gonna take to get there realistically? What do we, what's our best hypotheses on what the implementation of that looks like and what are the big bets we need to make? And then what's that gonna mean for how we need to shift our ways of being or operations as an org? And that's really all you need. And from that, you level up the key messages, and then the rest is change management. And then you can change that every quarter. You can change that six months. I mean, you can set a vision for five years out and regularly return to it. It's more agile, it's more flexible, and it really pushes leaders to get clear on what they think and make hard choices, which a strategic planning process, I think, lets leaders sometimes off the hook from making the hard choice. And not just the with E D or CEO, but like the whole team. Cause it's like the impetus is to add more and to get other people's perspectives and you want to please everyone. And so if it's just you and me in a room or you and me and your two people, and I can ask the hard questions, leaders will reckon with what they really think, and then they got to go test it and make adjustments. But that reckoning is a key part of the process, I think. And I think it's about too like where you bring people along in the process. Like, I think sometimes this the traditional process encourages this really wide funnel at the top, and people share all these perspectives and then they and then we don't know exactly what happens to them, versus a leader and the team bringing in what they already know, the dots they've already connected, and then creating some hypotheses around that and then getting input from that. It's a lot more honest, I think, because I think what sometimes happens is we do this big funnel and people say a bunch of things, we say, Yeah, yeah, yeah, we heard you, we heard you, and then we go and make a decision we were gonna make anyway. And then people feel disenfranchised. And actually, let's just be honest about where, where we want perspective, where we invite it, what we've already kind of decided, and then like get really clear on what are the hypotheses we need to test, and then get close, you know, get the people most proxible to the work to support that. So I think it can be simple. And what I end up creating with a lot of my folks is like, you know, eight-page document that's just like super clear, and it can be cut down to like one page where you can then you have like the key messages and you're just saying them over and over to funders, to your board, you know, to your team. And then that's really like the rallying cry that that drives, I think, real change. And I think because it's less of an investment of time and money, it's also like there's more flex in it inherently, which is because things are crazy right now. Things change.

SPEAKER_01 6:31

We know. The board and leader be more aligned. One of the things, the reason we started doing, you know, supporting boards on leader evaluation was that we were hearing from leaders we were placing a year or two after they were put in seat and they were like, Christina, can you get my board to evaluate me? Like, I don't know how I'm doing, or boards coming to me. We place this leader, and now we've realized a year later, and we haven't really done anything since then with them around like what are they supposed to be doing? What are their goals? What are the measurable outcomes we expect to see? You know, how are you doing on your own growth? Like, you know, one of the things I always say with a big search is one of the nice things we have is we have a lot of data about someone. Once we finish, you know, a leader and executive director, CEO hiring process, we've gathered a lot of information about them. But are we using that, right? As we think about their professional development plan and where they need to grow and what they want to get better at and, you know, what they're gonna do going forward. And so that's one of the things that we really like to work with boards on. And what I like with what you're saying is if you're forcing already the groups to come together with some really tangible KPIs and goals, that's gonna make everyone be on the same page. So there's less likelihood that there's a disconnect between the different audiences and what we're trying to achieve.

SPEAKER_00 7:40

Yeah. I'm really curious actually, you know, when you bring a leader into an organization, like how often is it that you that they want to see a plan in place that they can implement versus like come in and clarify a vision? Obviously, it's hard to step in somewhere brand new and do the work we're talking about. So is there a one-way or amount of time you think someone needs to be in seat before they are doing their own version of strategic clarity versus the board?

SPEAKER_01 8:05

Love that. That's a great question. I would say it varies. I would say one thing that we always talk to the board about in the beginning is we should be clear from the time we're launching the job and talking with people about the position, we should be clear about our expectations. So sometimes expected, like this org, you know, some boards will say to us, like, this org is running well. We've got a plan, we've spent a lot of time thinking about where we're going. We of course want input and insight from the leader, but we're not looking for major change. Some organizations are like, we're in crisis or we're in a turnaround and we don't have a clear strategy, and we need someone who can come in and kind of help us really drive our strategic vision. So we just try to be clear from the beginning with boards about that because different individuals are more or less comfortable or um interested in different scenarios. Some leaders are like, I don't want to have to create a whole new strategy. Like I want a place where I feel like they've got a really good picture of where they're going. And other leaders are really excited about that blue sky change world. Yeah. So I that's the first thing I would say. But the second thing I would say is I most folks I think are a little bit in the middle where they have a direction that they want to go in. But, you know, and we always say, like the new leader, they I don't know how you think. I think they need six months to a year to figure out what's even going on internally to really create a strategic direction.

SPEAKER_00 9:21

I agree. Yeah, most people that I work with have been in seat for a while and are looking to shift what they they're they're because you do, you need time to onboard, you need time to get historical context to really get to know the people and the players and understand where we've been and what we've learned, you know, what's been really working that we want to preserve, what needs to change. It's hard to do that when you first come in. Um I think it builds, you need to build trust with your team. To be able to do strategy this way, you have to have a lot of trust, right? Because you're not relying on this external complex process to build the trust. You're relying more on your own intuition and um perspective and then bringing people in on the lawn with you to support and drive it.

SPEAKER_01 10:02

So I guess if we think about takeaways, I have one idea, Leah. I'm sure you have something too. I think the thing, and I'm always a broken record on this, but you know, what I would say is if your board isn't meeting with you on a quarterly and then annual basis to talk about your goals and metrics for success and what we're trying to accomplish together, then we're not really doing governance right. And board members shouldn't be in the weeds of the work that's happening every day. They shouldn't be involved in like hiring of the average staff member. They shouldn't be involved in like day-to-day decision making, but they should be meeting with the leader on a regular basis to kind of look at where are we, where are we going, and how are we doing. Um, because I think, you know, either people sometimes have a dashboard with 30 metrics, which is useless because you can't look at 30 things in equal measure, or they don't look at all. But kind of how are we deciding those organizational health things that we're looking at? Maybe their numbers, maybe their narrative, maybe their sentiment. And you know, it can be, it doesn't have to just be data on a page, but there's something we need to be looking at on a regular basis to see if we're on track. And so that's the thing that I I think. And then I'm curious what your big takeaway would be for people.

SPEAKER_00 11:05

I say, like, if I were to talk to every single member of your leadership team and ask them, what's your North Star? Where are you headed? What needs to be true in three to five years, and what are the big things you're focused on? Would you all say the same thing? And most of the time they say no. And and again, it's not just about the document. Then you got to actually bring people you know along. I do, I like run workshops where we get everybody on the same page, understand what the misalignments are, where they need to be fixed, and that changes everything. And you know, if something new were to come your way, would you know immediately whether to say yes or no to it? That's another like good check. So there are like these checklist items, but that that first one I think is like the number one diagnostic of strategic clarity. And sometimes people are like, yeah, it's been living in my head and it's not on paper. And no wonder I think people are focused on the wrong things or there's friction between teams. So I I'm excited about this idea and getting people on the same page so they can do the great work that they're that they want to do in the world. Awesome.

SPEAKER_01 12:13

Well, Leah, where do people find you if they want to learn more about your insights or follow you in different channels?

SPEAKER_00 12:19

Yes, you can find me on LinkedIn. Um, that I post a lot there. I also have a substack newsletter called Leadership Material, um, which is really about the intersection between our own inner personal work and the external role of leading. And a lot of this stuff comes up here. And of course, on my website, which is LeahEisenberg.com, is another great place to find me too.

SPEAKER_01 12:42

And for me, it's agility search.com is our website. Um, I'm also on LinkedIn and I co-host the Higher Ground podcast with Josh Shuprik, and I also have a Forbes Business Council um thought leadership page. So look at me there, but everything's connected on LinkedIn. So find me on LinkedIn, you'll see it all there. Thank you so much, Leah. This has been a great conversation and hopefully help people feel a little better about how to get some strategic alignment and get everyone on the same page. Absolutely. Thanks, Christina. This was so fun. Can't wait to do it again.