How to Align Your Executive Leadership Team Around Your Startup's Core Strategies

Updated: Nov 5, 2019

Team tug-of-war. Executive misalignment. Toxic territorialism.

Sound productive? Doubtful.

Sound familiar? Likely.

You're not alone - the unfortunate reality is that most leadership teams are not fully aligned. The upside is that your company can separate itself from the pack if your team starts rowing in the same direction. With that in mind, we sat down with one of our members, Dane Atkinson (serial entrepreneur and CEO of Odeko),who broke down a few ways you can ensure your executive team aligns around your company's core strategies.

Signs That Your Team is Misaligned.

Before you dive right into potential solutions, a good first step is to diagnose your current leadership team and understand if you are aligned today. Dane points out two key indicators of misalignment that you can look out for:

1) Fiefdom wars and active territorialism

"What you'll see is shadow companies form inside your organization where teams begin to sabotage other teams. Without consensus in the exec team, others are forced to focus on their own priorities and success. When you're sitting in a room like that, you can feel the territorialism across your team where people defend and fight for what they're responsible for and own."

2) Indirect feedback channels

"Another big red flag is when there are backchannels for negative commentary on other execs. So as an example, you get pulled alongside by another exec who says things like:

- This other person just really isn't an exec

- They are not hiring enough people

- This person's team is not doing that great

All that is happening outside of the general conversation your team is having. They are not comfortable discussing these problems together because they are not all aligned, so they say it separately."

Three Best Practices When Aligning Your Team Around New Strategies

Now that you’ve determined if your team is aligned, it’s time to implement a few best practices to either solve your problem or improve your current situation. Dane identifies three best practices you can use the next time you’re aligning your team around a new strategy:

1) Get individuals to buy in first. Then focus on team alignment.

"Remember - humans are resistant to change. What has worked for me is to not have the expectation that I can change people in a single shot. I understand the need to pull aside different members at a time and get them to feel ownership of different parts of the new strategy. It may seem like a lot of excessive work, but it's so much less than trying to win everyone over after you've already dictated a new strategy. Spend the time upfront to get individuals bought in and then bring it to the table together."

"You have to make that extra space, especially if you know that people are going to be highly resistant to the new shift because you've shifted four times in the last three weeks or because someone is entrenched in a specific model. Getting them onto your side first helps. It's a bit of politicking, but it makes the buy in so much more legitimate because it's been preceded. It's a rollout strategy into your own executive team - you have to have your own release plan for your strategy."

2) Communicate. Communicate. Communicate.

"As CEOs, we tend to under-communicate, even though we think we are over-communicating all the time. I like to say things so much that people finally tell me to stop or I ask them to say things back to me. I'm always surprised how little I am able to transmit from my brain to others’. If you just do one lunch and an exec team session on a whole new direction it's easy to think - yeah, it's all sold! Well, two of your execs aren't going to be and will have thoughts like:

- It feels like we change our strategy every week so I'm just gonna stick with my strategy.

- I'm going to second guess the company strategy entirely.

- I want to build for the future that I think they're going to realize they need down the road."

3) Experience levels matter.

"For the most part, senior executives will understand the importance of alignment. Even if they're in violent disagreement with your strategy, they still will play the unified parent front where mom and dad agree, even though dad doesn't agree with the policy. For less mature executives, you can't muscle it. It just doesn't work. You can't be in the room and just say: we're going left, I understand there is misalignment here, but we're going left. You can't expect that they are going to hold that story out to their teams, it just won't work.

It doesn't mean that those execs aren't highly valuable producers and at the stage of your company, that they aren't what you should actually have. It just means you need to spend the extra time understanding their reasons, explaining your reasons and getting them to buy in. Because if you walk out of the room with false alignment - sure boss we will go left. Their resolve will crack. It will leak out into their teams and then it will leak out into your company."

Tactics When Adjusting Your Team

The unfortunate reality is that sometimes adjusting your executive team is the only solution to your alignment problem. Dane highlights three things to keep in mind as you look to make changes to your team:

1) When is the right time to make a change? Probably last month.

"I've actually learned this from Venwise - when you start to rationalize your concerns around a team member with other people, you're already past the place where you should get rid of them. If you have a team member who you're no longer discussing this struggle with, but you brought it up to your peers, it usually means you're already past the point of being right and just have to face the hard fact that you need to make the change.

That sounds super easy. It's not. We've seen this in your roundtables for years where someone is clearly past that point. It usually takes two more sessions before people get up enough momentum to make the change. The rational is that these are very hard to fill roles and a lot of time there's specific nuances to it. But, if your execs can't upwardly manage the CEO to at least not want to fire them, it's a really bad sign. That probably means they can't laterally manage either. It is a considerable red flag if they can't keep you participating in that conversation. If that’s the case, well, it's probably not the right fit."

2) Don't underestimate the value of a trained executive.

"I think a lot of companies underestimate the value of a trained executive. Before replacing someone, it's worth seeing if you can retain that person in another role. What I do is create a portfolio analysis of the skills our team has and build job titles as a combination of those portfolios. As an example, we'll take a CTO (a very amorphous title) and have a conversation around them being great in architecture design and team culture, but mention they've not been great at hiring and these other two things. So we want to make that CTO the Head of Architecture and get somebody in who can take on those other missing skills. If you can salvage them to be a valuable asset for your company, you can get a huge boon for business.

Another red flag is someone who's holding on tight to every part of their title. If you’ve done the above, you've at least started the conversation by letting them know they've excelled at certain things and we value these things, but as we grow, we need these other categories to be stronger. If they don't want to step into those and focus on what they’re good at, then they'll probably have to find another place to make this work. You're not approaching them from the perspective that they are failing in their job and we need to hire somebody else. You're at least making an attempt to get them there and recognizing that they have likely done very valuable work for your company."

3) Don't just hire for the role. Hire for your executive team room.

"When hiring new executives, we put too little weight on how they participate in the exec team room and much more weight on how we think they're going to do in their actual job. A bad personality really can disrupt the room's productivity and the company's as well. In our interview process, we do one sort of group thing, but it would be cool to extend on that. We bring people in as advisors and have them sit around with the exec team for a few meetings to take notes, but it would be kind of fun to add that heightened pressure in the room and see how they really react."


When it comes to team alignment, we think Dane summarizes it best:

"It is an extremely hard thing to get right and at the same time it's one of the most important things to get right."

We hope this post arms you with a few tangible takeaways you can implement the next time you're aligning your leadership team around large strategies. If you're looking for more best practices from other high growth execs, subscribe to our monthly content newsletter where you can stay up to date on how other execs are solving some of their toughest business issues.

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