Leading a team of owners: the importance of critical thinking and leading a team that creates its own charter

I believe a company’s success is not in one person’s hands, it’s always best distributed, empowering the individuals on the ground to make the right decisions, so that the company’s products and businesses don’t have one owner, but many owners, creating a culture of lasting impact.

One of my favorite moments is when someone on my team comes to me with a great idea, and describes why it would be amazing for members and drive significant impact. As a product leader, I look for these moments, I want our teams to come up with well thought out plans they have conviction in - given they’re closest to customers and on the ground data I firmly believe they have the best view into what has the potential to move the ecosystem most meaningfully. But getting to these moments is not the teams’ responsibility alone - it’s my responsibility as a leader to provide the right environment and space to make this a reality.

Here’s the tips that work for me (disclaimer to please not pass too harsh judgement ;), and I’d love to hear what works for you!

Tip #1 - Be comfortable with ambiguity.

As a product leader - I see my responsibility as focused on “where we’re going”, and I look for the team to figure out “how we’ll get there”. That requires leaving ambiguity on the table and not have all the answers - while this is extremely uncomfortable at times, and often requires the leader to not have the “this is going to look like x, y, z” answers at hand, by leaving ambiguity on the table we’re creating space for the teams to step in and draw how things would look like, allowing them to come up with their own plans and ideas.

Tip # 2 - Encourage your team to disagree with you - yes! You heard it right! And then come up with their own strategy and roadmap, consistently.

Building an independent team requires critical thinking from all individuals. No one person will have the right answers and the last thing you want is have your team be dependent on you/any one person to draw their roadmaps. Part of critical thinking is evaluating ideas and developing a data driven sense for what would work and what would not. An important step towards that is to encourage critical thinking on the way to have the team feel full ownership over their roadmaps, their impact and their path. Here’s how I encourage it - I share an idea with the team, and see their thoughts - if someone comes back and says “actually, that’s not going to work”, I say - “great, so I’m looking for you to tell me what will”, and l give them time to circle back, next time - I’d love them to not only explain why my idea wasn’t going to work, but also what we should do instead.

Another thing I like to do when sharing an idea and hearing a “yes, we’ll do it”, is asking “what would be the impact, is it worth while pursuing?”, I don’t want the team to do things because I or anyone else said so, I want us to pursue ideas because they’re going to create impact.

Disagreeing can be hard, especially with someone more senior than you, so I try to normalize the culture of disagreement by making jokes on “being a team of rebels”, and “the team who’s not good at following rules”, there’s an underlying motivation there - I want the team to know it’s okay to disagree, and then form the right path, critical thinking is healthy.

Tip #3 - Stay out of the details.

The road to driving impact is not built on a few good ideas, but on many iterative tests and learnings building on each other - the more times we go to bat (experiment), the more chances we have to create impact. Once you’re running hundreds of a/b tests, my involvement in the details as a leader will slow down the team rather than accelerate, if I’m less involved, the team feels more empowered to come up with solutions, feel ownership knowing outcomes were driven by their own decisions and therefore they’re full owners of outcomes. I no longer own our team's goals in this model, the team owns their goals. That’s a positive since if things don’t go well, they’ll also want to make it right, and when the leader is not there - the team continues to be self sufficient.

Tip #4 - Provide coverage for the team and the opportunity to make mistakes safely.

Being not in the details and having less reviews means things can be less perfect and mistakes can happen. To operate freely the team needs to know you’ll have their backs if mistakes do happen and there’s no negative outcomes, as such, if something arises in a ramp we did - it’s my job as a leader to say - “got it, ty for the feedback, we’ll address”, and that’s it, there’s no negative consequences to making mistakes to individuals on the ground. When scrutiny is too high, analysis-paralysis happens, and the team needs you to confirm and sign-off on things being afraid of implications - that takes away their autonomy, significantly slows the teams down, and is a negative overall.

Tip #5 - Manage to outcomes, not to projects.

While roadmaps and plans are good, the reality is some would work out, and some won't. Once there's a culture of holding teams accountable to specific activities/commitments - they'll prioritize making these activities / commitments happen ('what we were asked to do/accountable for') vs meeting the final team goals/committed impact. In order to increase our chances of hitting our commitments, we have "loosely held roadmaps", what these means, is that if "plan A" didn't work out, you're free to pivot and do something else at any time, if that something else will have the impact one needs to meet it's targets. I don't hold the team accountable to projects (that would not empower them to be autonomous high impact teams), I only hold teams accountable for results they committed too - they're smart and will find the path to get there on their own, and need the flexibility to adjust plans based on learnings to get there.

Tip #6 - Be consistent so the team can know what you’d say and do when you’re not in the room.

As you’re not going to be in all discussions and decisions - you want the team to know how you make decisions and follow that when you’re not in the room, that requires consistency. If the way you make decisions follows the same set of principles - the team picks up on that and can make decisions in a similar way. In our teams, we often run leads meetings covering ramps and learnings (which is, per tip #3, where I often see things we ramped for the first time - after they already ran and we already have data on how they performed) - the team can pick up there on what I ask and how I think, and make decisions based on that. That’s where “not always making decisions” is important too - if there’s no value add, or the decision / advice you’d provide isn’t consistent/can be applied to other scenarios - don’t provide it. Make it clear what you care about and optimize for - and also - what is not high stakes for you to have an opinion on, so the team can make similar decisions when you’re not there.

As leaders, we’d like to know what we do matters and makes a difference, and that if we weren’t doing what we do - things would not be the same. But that’s a trap! In success - our teams should be independent whether we’re there or not, and our success as leaders - is providing the right environment and tools for our teams to flourish independently, creating a culture that can live on, regardless of us.

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Opinions are my own only!