Hooked on Startup-Curious Leaders

Careers are a jungle gym, not a ladder - Sheryl Sandberg 

On the hunt for your next leadership endeavor and find your curiosity leaning toward a startup? We delved into this topic in our S Curves issue, discussing how to align career motivations with the growth stages of the business. But if you've spent most of your career building your experience at big tech, your biggest hurdle is convincing a founder you are the right leader for their startup.

What's going on?

The pendulum has swung. Only a few years ago, a big tech logo on a resume almost guaranteed an interview with a startup. But today, there's a great deal of founder apprehension — and, dare we say bias — to place a risky bet on leadership talent coming from big companies. This creates significant hurdles for startup-curious leaders to put their experience to work in a different way — even when they crave reinvention. But just because there's curiosity doesn't mean these leaders can embrace the reality of what it's like to be at a startup where there's no place to hide and everything is exposed. Misalignment can often lead to organ rejection where leader and opportunity aren't appropriately aligned with the amount of hands-on work that’s required. But for those startup-curious leaders who possess the ability to scale down their functional experience and thrive at a startup, opportunities to demonstrate your abilities may still be limited or never happen at all for various reasons. Maybe you inadequately connect how your experience converts to your startup stage of interest or don't brand yourself appropriately. Often, founders cannot identify or qualify "conversion DNA" or discount anyone coming from big companies immediately. One or all of these things can lead to missed talent opportunities for both sides, but we'd like to address what’s in a curious leader's control.

Why does it matter?

If, as a leader, you're having difficulty connecting how your work can transition to a startup, we 100% guarantee a founder will, too. Take steps to map your journey and increase your odds of being noticed:

Step one — Find your sweet spot. Take the time to identify and isolate the meaningful ways you've delivered impact. Map your work to the growth stage (seed, series A, B, C, etc.) you are targeting. This exercise should yield connection points between your work and outcomes relevant to the job you'll be doing at a startup. If you're coming up empty on details, ask why? If you find that 90% of your past work has been managing, delegating, or removed from what's happening in the trenches, ensure your current motivations are appropriately aligned. Are you ready, willing, and able to scale down to what is often a skeleton crew or, in the earlier days of startup, a team of one — you being the one? Do you have the patience required to scale back up over time? Because startups are so nuanced, you may find your bigger company experience is best positioned for later growth stages — where the function needs a reboot, and you can put your optimizing skills to work revamping teams, systems, or processes. Do some deep research to validate what "startup" means to you. If startup means 5,000 employees, it's time to regroup. You may still want the stability of a larger company but aren't being fulfilled in other ways (team, culture, work.) Maybe it's time for a slightly smaller team elsewhere versus a radical career transformation.

Step two — Articulate why you, why now. Tell the story of how your experience maps to a startup. These aren't high-level brag statements. They are data-driven examples demonstrating you can solve startup problems founders need solving. Build confidence that you understand functional issues intimately (revenue traction and repeatability, lead gen, product adoption, brand awareness, customer churn, etc.) and can produce the scaffolding and plan to attack quickly. Highlight key strengths necessary to thrive in the trenches — adaptability, critical thinking, curiosity, etc. — by tying this DNA to work you’ve done. And remember, startups need great functional leaders who are versatile athletes with strong business acumen. Especially early stage — where every decision made reverberates throughout the entire business. Demonstrate an understanding of your decisions' upstream and downstream impact and how you have lived with the consequences of your choices and actions versus just parachuting in and out, letting others deal with your disasters.

Step three — Be empowered. All too often, leadership candidates surrender their power to an interview process. They use the process to shape what they want versus knowing what they want and validating it through the process. Stop doing this. Be in charge of your journey. Showing leadership during your interview process is an incredible opportunity to demonstrate your leadership skills. Resist the tendency to give interviewing control to those interviewing you. It's a fact that there will always be more bad interviewers than good ones. Because of this, discovery conversations often fail to yield the high-value evidence that validates the ability to perform in the role. If you can successfully scale down, you’ll need to introduce real evidence during interview sessions. Canned questions lead to vague responses which in turn leads to low interviewer confidence. Open up your experience aperture with confidence-building examples, showing how you operate in the flow of work. This ensures an otherwise well-intentioned but unskilled interviewer comes away from the conversation with evidence you can do what's necessary to get the job done.

Examples in practice:

Canned Q: How do you analyze complex problems?

Demonstrate startup fit: Let me tell you about a time when I had to use a creative solution to address a complex problem. [How did you identify there was a problem? What was the scope? What data was missing? What solutions did you consider before choosing the path you ultimately did? What cross-functional implications were involved? What hurdles did you overcome? What specific impact did your solution have on the business?]

Canned Q: What is your preferred management style? 

Demonstrate your startup fit: Here's what I needed from my manager to succeed during various stages of growth at XYZ company. [Describe how much freedom and control you had in your role. Was it enough? Too much? Why? How often did you and your boss communicate? Often enough? Describe what you needed from your boss that you weren't getting. What worked well and why? How did you manage up?]

Canned Q: Can you roll up your sleeves? i.e., demonstrate you are in the flow of the work.

Demonstrate your startup fit: Let me give you an example of a problem I leaned into and solved as a leader. [Describe the issue, why you leaned in, your approach, and how you gathered information to inform direction. Tell the details of constraints you faced and both practical and creative ways you had to work to overcome barriers. Describe how you tested your solution was working and identified that you addressed the root cause. How did you know you went deep enough into the details to validate it stuck? Leverage data to tell this story.]

Canned Q: What are your strengths and weaknesses? 

Demonstrate your startup fit: Here's a complex problem/issue/broken process I had to solve at company XYZ and why I raised my hand to work on it. [Describe the kinds of skills you leveraged during the project. What parts of the project tested you and why? Where did you shine and why? Where did you need to ask for help? What was the goal versus the outcome?]

Canned Q: Are you adaptable? 

Demonstrate your startup fit: Let me tell you about a time when I stepped into a new role / took on a new responsibility without much (or any) training or preparation — a sink-or-swim experience. [Here's why it was hard (time limitations, business pressure, and other constraints.) I took X approach. Here's how I validated that I was working in the right direction or needed to pivot and the steps I took to ensure what I designed could flex to changing circumstances. Here are my key learnings and the skills I acquired along the way.]

What do others think? 

"Curiosity is a great signal that you're ready to explore a startup. I've loved my time working with early-stage and growth companies — both have played an invaluable role in my career. I felt I was generally well prepared through my experiences in larger tech to transition however, there was also a massive opportunity to learn and grow. Like any change, the most important ingredient is that you want it, are curious, and are willing to undertake the reinvention it will require. Start this journey by connecting to the startup community and VCs like Madrona through your network." - Ted Kummert, Venture Partner at Madrona and former Chief Product Development Officer at UiPath

"It can be challenging to identify a strategic leader who can also scale down. Many individuals who have been successful at big companies express a desire to be part of a startup, envisioning greater autonomy, decision-making freedom, and a reduction in red tape. However, they might not fully consider or anticipate the practical challenges that come with the hands-on, gritty operational leadership required in a startup environment. Getting honest about what you REALLY want is critical." - Bill Richter, CEO at Qumulo, Inc.

What do we think? 

We think there can be a ton of value in recruiting scale-down leaders who have lived through the levels of complexity that comes at various stages of growth and scale. This DNA can be a big win for founders but getting to this point requires curious leaders to do the intentional work to right-size where they best fit on the S Curve. Take the time to identify the problem you are working to solve in your own career first. Unpack that problem carefully and examine it to make educated decisions that will unlock your best work versus adding more career debt that you’ll have to solve for later.

What do YOU think?

Take Action

• Flip the Script. Our friend, Kendra Haberkorn, wrote this book filled with question examples and strategies. Our very own Shannon Anderson, Madrona's Talent Director, created a workshop inspired by Kendra's book - give us a shout if you'd like the links.
• Invest in a career coach to help you identify your career problem so that you can ensure you are startup ready.
• Big tech bias. For founders seeking their next functional leaders, remember there are diamonds in the rough who can scale down to scale back up. Be intentional about the process to validate two-way fit.

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