A Startup Advantage: Knowing Your Leadership Style

I’ve been doing a lot of phone screens for open roles at ClassPass and inevitably for the more senior roles the conversation turns to leadership styles.

Almost always when asked what their leadership style is they state something along the lines of: “Oh great question, I guess I haven’t really thought about it. I know I am not a micro manager and I believe in empowering my teams to do great work.”

Uhmmm. [Looks around]. Whatttt?

I appreciate the sentiment and I most certainly love hearing a senior hire’s commitment to empower but we need more. Now is the time to dig in and understand what is your natural leadership style? How could it benefit an organization? A culture? How could it balance out the existing leadership team? Perhaps most importantly, how does it manifest itself every day to drive results and succeed?

As a startup leader you can fundamentally change the course of a startup’s life. Your leadership style, when mixed with the existing culture, will either be a business advantage or an anchor.

So let’s talk about leadership styles. There are a million models and frameworks out there you can latch on to. One of the simplest and quickest to start with is Mark Murphy’s four fundamental leadership styles. His belief is that every leader has a prominent approach and it falls into one of the four styles below.

Fun little bonus [because I’ve had way too much coffee this morning]: As I walk through them I’m going to call out some pros and cons on how you can see these playing out in a startup tech culture.

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Pragmatist: Pragmatists are drivers. They have super high standards, and results matter most. Competitive, bold, risk takers.

Pros: Get’s it done, amazing ability to create a culture of accountability and OKRs rarely stand a chance against these types.
Cons: Can miss the cultural nuances required to inspire. Can over index on numbers and lose sight of the mission, purpose, customer voice.

— — —

Diplomat: Lead through teamwork, focused on culture and connection between stakeholders. Kind, social, conflict resolvers.

Pros: Can rally a team, create a strong “in the trenches” mentality, peacekeepers during stressful times.
Cons: Can lack the cut-throatness (shhhh…let’s pretend that’s a word) required at a startup. Can over index on dynamics at play and lose sight of the output needed.

— — —

Steward: The rocks of your organization. Incredibly loyal, ready to help at any time. Stable, and dependable.

Pros: Always get’s it done, you can throw anything at them and they will lean in and learn it. They do not give up, they exude hustle.
Cons: They can miss the big picture, sometimes they fail to raise a hand and ask “but why?” which is key in being efficient and effective with our startup time.

— — —

Idealist: Visionaries, high-energy types. Positive forces of nature. Eager to learn and grow, charismatic. Driven by their intuition, open-minded.

Pros: They often have the crazy idea, the founding “something” that makes others jump all in. They can carry startups though the tough times with sheer idealism.
Cons: Not strong operators, or process drivers. Tend to over index on customer needs and fail to see business needs.

— — —

Okay. Now that we got that all out there, you can see why it matters — especially at startups. The harmonic energy among a small team trying to make something out of nothing is so critical. It’s importance might only be trumped by finding product market fit, in my opinion. Because as we all know, if you’ve got the product, you need the team.

The team at a startup is everything. The mission, the customer, the results, the culture — it’s all created, cared for and shared with the world…by your team.

So next time you’re asked what your leadership style is perhaps you can throw one of these out and create a meaningful dialog about how you can be additive to the culture. It’s a great time to brag a bit about how it plays out, show them the pros, get honest about the potential cons, and ask for the support to round out those edges.

For those wondering, I am a Diplomat with a pulse line of Pragmatist. And over the years I’ve realized I work best for Pragmatists but love to follow Idealists. My teams tend to be full of Stewards but lead by Pragmatists and all of that comes to together for a really great vibe. One I’ve learned to build and nurture to create my highest performing teams.

That’s just me though. You gotta do you. But to do that you’ve got to know what you’re working with. In fact here is a two minute quiz (I am not kidding, time it!) to find out our style…go on, you know you want to.

Happy Monday guys, let’s make this week count. #highfive