Hooked on the Advantage of Leadership Role Calibration - Issue 25
"The greatest obstacle to discovery is not ignorance; it is the illusion of knowledge." — Daniel J. Boorstin
Through all the ups and downs of the market, one thing remains true — the best leaders are always in demand. And when you consider the precious number of opportunities you’ll have in front of these leaders, the last thing you want to do is show up to that conversation with a half-baked idea of what you need and why.
What's going on?
It happens all the time — taking a leadership role to market before it's been thoroughly vetted. Even when your team is in agreement on the problem to solve, the simple fact is, you don't know what you don't know. And it may seem harmless to calibrate on the fly — blowing through conversation after conversation with candidates, revising the spec as you go. But this "I'll know it when I see it" strategy is painful — wasting valuable time, wrecking your talent brand, and sabotaging candidate experience in tandem. Not taking the time to stress-test your role spec sends you down the path of investing too many cycles with leaders who are misaligned. Or worse, the right leaders opt out due to lack of clarity and poor value prop positioning — unable to connect how the problem you are trying to solve is the very challenge they want to tackle. This pain doesn’t have to be your reality. But it requires you invest more time on the front-end with subject matter experts who can fill the gaps and help you dial in what good looks like in the role.
Why does it matter?
Using the interview process to calibrate the spec is a costly endeavor. It's like building a product without first talking to customers — you can get a lot wrong and a couple things right. Calibration conversations serve as your leadership hiring "sandbox," giving you space to test the positioning of your role, ask what you’re missing, gather insights, and get objective feedback before stepping into conversations where impressions are your currency. This feedback helps you iron out the kinks, gain more functional awareness, and hone your pitch so when you do get great talent on the hook, you can confidently articulate the opportunity impact they can make at your startup. And this ultimately unlocks the ability for candidates to answer why you, why them, and why now.
What do others think?
"As a founder, when hiring for a position you've never hired before, it is so important to start by speaking with successful leaders and people in that role. They will be able to provide insight into what makes a great candidate and what you should be looking for as part of your interview process. Ultimately, it helps ensure you can rapidly hire the right person and increase the odds they are successful longer term." — Fabio Fleitas, Co-founder and CTO at Tesorio
What do we think?
While every candidate conversation will bring insight, these insights should validate a leader's fit for a role rather than help you design it. If you are still questioning the spec design, you have more front-end work to do on your hiring blueprint. And depending on your functional expertise, you may need to invest more time gathering insights and advice at the earliest stages of your spec building process. That's okay — just remember to recalibrate before you launch into candidate conversations. This will give you a competitive advantage — ensuring you put your best foot forward when it matters most.
What do YOU think?
Take Action
We recommend a minimum of two to three calibrating conversations leveraging your network of calibrators. This ensures you diversify feedback and perspectives.
Investors: Leverage your board and advisers as first-pass feedback on the spec. They can make introductions to quality executives who aren't necessarily looking but are the target blueprint for what great looks like. Sometimes these connections lead to conversion. VC talent teams can help guide leadership spec work, make intros, and provide feedback.
Experts within your network: Connect with leaders in your network who have functional expertise. Not only will they have insight, but they can broker second-tier connection conversations.
Extended network: For any leader already in seat at your startup, ask them who the best [engineering, product, GTM] leaders are that they've worked with. Get the intro and connect!
Industry leaders: Connect with leaders in your industry who do this work now — ask for advice.
Peer network: Tap your extended VC founder ecosystem. There's a wealth of experience to glean from other founders who have been through similar journeys.
Mentors: Mentors have overcome similar challenges and can share valuable insights on hiring strategy, questions to answer, and landmines to navigate.
Strategic search firm partners: Search partners are deeply plugged into the market and can provide insight and lessons learned through other search processes. Plus, they can validate your spec and encourage you to open the aperture if your spec is limiting the universe of potential talent.
Tools, Events, Insights
Aspiring for Intelligence → Snowflake vs Databricks
AI Tinkerers Seattle → July Meetup
Hey! Entrepreneurs —> Take the Leap!
Madrona Insights —> A Wave of Personal Agents is Coming