Leveraging Leadership

Worth The Fight? Juggling Short-Terms Wins and Long-Term Goals

• Emily Sander • Season 1 • Episode 154

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Emily Sander talks about deciding which battles to fight in a leadership role. She shares a story of a Chief of Staff who chose a short-term reorg plan to avoid conflict with a long-standing Chief Product Officer. Another example is a CEO who decided to replace a problematic Senior Vice President to prepare the company for a sale.


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Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 


Time Stamps:

00:40 Example 1: The Reorg Proposal Dilemma
03:21 Example 2: The CEO's Staffing Challenge

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In this episode, I want to talk about the question, is this battle worth fighting? as a chief of staff and as an executive, sometimes you have to ask yourself, is this battle worth fighting? Is this a hill worth dying on? I was just talking to a relatively new chief of staff and she was tasked with coming up with this reorg proposal, like coming up with options for this reorg proposal for this one major area of the business. And one of the main teams within that area was the product team. And. The chief of staff and I were discussing this and basically there were like two options. Option a was to propose significantly overhauling this product team and option B was kind of doing this interim step of like, let's do this adjustment. And that's a totally fine, solid answer for now. And then just everyone understands that at some point in the future, we'll have to make a further adjustment. So that was kind of option a option B on the table. Um, Some information about this, this chief product officer who led this product team, they had been there since forever. So they were a founding member of the company and um, they had several loyalty members who felt very protected by being on that team and kind of felt like, Hey, we're the king of the castle cause we're on the product team and this is our leader and so no one can touch us. So that type of thing. Another data point is the chief product officer was, Legitimately going through a lot of change, like a lot of change was happening around them and the company with their role structures, new team members, et cetera, et cetera. So, um, definitely kind of like defaulting back into like, you know, this is mine and this don't touch this and don't rattle my cage anymore. So that's kind of the scenario there. And this chief of staff and I were having this conversation and it was basically, basically the question of like, is this worth it? Is this battle worth fighting right now? Um, option a is going to set that team up for long term success. That structure is going to set that team up for long term success. Option B is going to set it up for short term success. Yes. And then need to be adjusted later on. And at one point of this conversation, this chief of staff was cracking me up and was like, so basically the question is, if we take their ball away, is the tantrum going to be worth it? Like, is the tantrum going to be so bad that it's not worth it right now? Um, which was like, not wrong, which is like, not a, not a inaccurate way to describe it. And the decision the chief of staff came to was it's not worth it right now. With everything going on with the chief product officer, with everything I have going on across the company. With the fact that we have an option B that's totally viable. This isn't a hill I'm going to die on. And so they went with option B, they proposed option B. So that's an instance where like, Nope, not worth, not worth it. Not right now. Move on. Second example, I was working with a CEO and, um, they had just not just, they were about 18 months in to being a private equity backed company. So they had taken on PE investment and this particular PE firm typically held for about five to seven years and then would sell the business again. So the CEO's job. Was in the next four years, get the company in position to be sold, make it attractive, grow the company, grow the valuation, all those things, dozens and dozens of things go into that. One of which is having a strong leadership team is showing that you have the people in place to do the job and to scale the business. Oftentimes the. The people who start a company are not the best people to continue leading that company after a certain stage. Can people do both? Absolutely. Can people make that transition? Absolutely. Is it sometimes like, hey, I ran my leg of the race and now I'm handing the baton off to someone who's good at the second leg of the race? Yes. And so we were talking about all the, all the executive team members and there was this one SVP. So senior vice president who ran a very important, um, team and long story short, they had become a liability. And they had become more trouble than they were worth. And they had tremendous industry knowledge, had been in the industry since forever, knew everyone, had connections, network, knew the like players and like the nuances of the industry, all of those things. And that's. Honestly, that knowledge and that expertise kept them in that role for so long, but it got to the point where, Hey, at this stage of things, um, we need someone who can interact and communicate with colleagues. Um, At a, at a more professional level. And I just had a different level of leadership. And so the CEO and I were talking and this question came up with like, is this worth it? Is this battle worth fighting? This person, um, if this person left like tough conversations, we're going to have to be had with them. Tough conversations. We're going to have to be had with their team members and with certain clients. This would get around the industry. So different like partners and different players within the industry. Probably would have to have back channel conversation. So it was, it was a significant move, but the CEO got to the decision of, I need to do this now because then I can get a new person in and get them up to speed and up and running in time to make a difference In this three, four, five year period, I have to get the company ready to be sold. And I can't have this liability and I can't keep dragging it, you know, to the next milestone and hope it gets better, hope it gets better. And then it doesn't. And we're stuck with this when we're trying to sell the company and people are vetting everything, including the leadership team. And we have this, you know, this, this, uh, you know, this liability standing out amongst our team. And in the end, the CEO came to the decision of, look, I have to address this now. Like this is a battle worth fighting right now. because I need the time, meaning I need to get a new SVP in there that takes a while to recruit and hire for, I need this new SVP to get up and running, which at that level is like 12 months plus. And I want all these, the teams and the customers and the different, um, industry players to kind of. I want time to have these conversations for the dust to settle and then for the new SVP to take over. And then it's just the way it is for two, three, four years going into the next sale. And so that was something timing wise, it wasn't going to be pleasant, but it had to happen. And so it was a strategic battle. The CEO was going to take on now. So in both of those examples, it is asking ourselves, is this a battle worth fighting? Is this a hill worth dying on? right now. And sometimes the answer is a strategic no. And sometimes it's a strategic yes. so asking yourself these types of questions as you go through your day and your week and your month and being thoughtful and being strategic and seeing all of what's in front of you can be really, really useful and effective. So I'll leave you with that and I'll catch you next time on leveraging leadership.