Recruiting for Organizational Resilience
Navigating Culture Change – Part 2
My specialty is helping startups navigate transformative change on the path from $10M to $100M in ARR. Over the course of this quarter, I’m exploring a question that’s been bugging me for years: Why aren’t we hiring leaders based on their ability to build teams of lieutenants?
This post is part two of the subseries on navigating culture change as you scale. Read part one here: Rigid, Robust, or Resilient.
Over the past ten years I’ve refined the recruiting principles behind building a successful team of upwardly mobile lieutenants. Today, I’m going to share the guiding principles behind how I interview and hire.
These are the principles that allowed me to identify and hire middle managers who surpass their own expectations.
For example, among the lieutenants I hired at Pantheon:
Less than 3 years later – one of those middle managers is doing my old job.
Another moved from sales to product and kicked ass on both teams.
A third unlocked a partnership that single-handedly moved the company into winning more Fortune 500 customers.
And a fourth co-founded an AI startup :-)
Today’s cover image is Leonardo Da Vinci’s Last Supper. Here’s why I picked it:
Without the twelve disciples (i.e., upwardly mobile middle managers), Christianity wouldn’t have spread outside of the Middle East. Without one of those disciples (Peter) setting the religion on a path to global dominance (i.e., graduating from start-up to scale-up), it wouldn't be where it is today.
I. Hire for trajectory, not expertise.
I like to look for a track record of fast and continued growth – erring on the side of hiring people who are slightly junior but have grown quickly over the past 3-5 years. I’d rather hire someone who will need 6 months to fully grow into the role… and then overdeliver in 12 months – instead of hiring someone who will perform “at expectations” on day 1….and still be at the same level on day 365.
Crucially, this also supports DEI goals and ensures you build a more diverse team.
When you hire for expertise (i.e., people who’ve been there and done that), you’re implicitly inheriting the hiring and promotion biases of leaders who came before you – you’re limiting yourself to a talent pool that’s been constrained by the societal biases of Gen X.
But, when you hire for trajectory and potential – you get to shape your own talent pool, free of those biases.
II. Seek out intrinsic diversity of thought.
Our experiences shape our thinking styles, biases, and operating norms. But those experiences come in two flavors: those that happen to us (e.g., growing up in a different country or landing a job after college and sticking with that career track until now) and those that we seek out (e.g., choosing to do an internship aboard, switching careers half-way through). It’s this second type – especially when it’s driven by an inherent desire to seek out challenges that matters.
I look for people who purposefully stretch themselves out of their comfort zone – and do not necessarily present a linear narrative. When you combine this with hiring for trajectory, you start honing in on candidates with highly transferable skills.
Candidates who have been successful in multiple industries, functions, and business contexts are likely to continue to grow, adapt, and go further as part of your team too.
III. Don’t be afraid to hire a “mini-me.”
I’ve often been cautioned to avoid confirmation bias. There’s a popular belief out there that hiring people who think, behave, and have similar foundational training to yourself is a sign of close-mindedness on behalf of the leader. But the context matters here.
As a leader, your middle managers are there to make you more effective. It’s critical that you understand what is required for that.
If you’re wasting cycles figuring out how to align your communication styles – you can’t be effective. If your lieutenants convey information in ways that make it harder for you to pay attention – you can’t be effective. If the people you rely on like to figure out things as they go, while you need to plan everything ahead of time to sleep well at night – you can’t be effective.
Of course, this needs to be balanced with principle II above (hiring for diversity of thought).
IV. Don’t interview – collaborate instead.
The traditional interview (“Tell me about a time when…”) is a crutch. A crutch meant to cover for the fact that most people can’t communicate clearly in writing.
Without the aid of back-and-forth Q&A most candidates can’t put themselves in someone else’s shoes and summarize the outcome of the work they do in a few bullets.
You shouldn’t be hiring people who can’t communicate in writing to be your middle managers. One-on-ones don’t scale and group meetings are a nightmare: concise written communication is a requirement for future leaders. A good resume should answer most of your “Tell me about a time when…” questions.
Instead, focus the live interview on simulating real-life collaboration instead. There’s a reason consulting companies like to do case interviews: it is the best way to approximate the real work they do. I like to take it a step further and simulate a 1-on-1: bring a real problem, work through it together for 30 minutes, evaluate if the candidate held up their side of the conversation and pushed your thinking forward (see principle III above).
V. Hire relationship-builders, not team members.
There’s a lot of value in building out a well-rounded team where each person will lift up the others. That means being thoughtful about the skill set and experience each person brings, balancing out seniority and backgrounds, and creating overlapping mandates.
But the reality is that most startup teams go through a material transformation every 12-18 months: leaders get promoted and move into bigger roles, a single-point-of-failure person leaves, responsibilities get reallocated, former peers start reporting to each other, etc.
How do you future-proof your hiring in this context?
Look for people who are great at building one-on-one relationships independent of the hierarchy around them. People who’ve been able to come into any team and made others around them successful, then looked around and reached across the aisle to other middle managers in the rest of the org. (For more on this: read The Magic of Middle Management.)
Is this article hitting a nerve?
Consider sponsoring a 1-on-1 coaching engagement with me for your high-potential middle manager. Together, the three of us will work through a structured program that’s proven to remove their ceiling and enable you, as their leader, to do your best work.
Alternatively, if you’re looking to unlock the next phase of growth for your team and company, I offer project-based strategy & advisory work for Founders & CxOs. Together, we’ll work through your strategic options, close your go-to-market gaps, and elevate your team.
Why does all of this matter?
For an outside example, look at Upwork. As I mentioned in my last post, over the course of 5 years, Upwork went through a massive transformation – while retaining its culture, mission, and heart. Some more context:
The company formed through the merger of two competitors: Elance and oDesk,
Went through a near-concurrent CEO and CFO transition,
Saw growth fall off a cliff, bottom out, and re-accelerate again,
Built an enterprise sales team from scratch,
Put in public-company-grade processes and had a successful IPO.
Three ingredients made the culture – and organization as a whole – resilient through all of it.
A middle management layer with shared norms
(Hiring principles III & V)
During the crucial scale-up years, around a quarter of Upworkers had come over from eBay (myself included). At the same time, the leadership team brought in key operating norms and habits from other current and former Silicon Valley leaders: Google, Microsoft, PayPal, Yahoo.
A deep bench of cross-functional talent
(Hiring principles II & V)
Top performers constantly moved from Analytics to Operations, from Marketing to Product, etc. When revenue growth decelerated and budgets tightened, this trend accelerated further. Cost and hiring constraints forced leaders to proactively think about their organizational design in order to maximize the impact of top talent across the company.
Leaders that developed multiple lieutenants
(Hiring principles I & IV)
Most leaders had more than one deputy and a potential succession plan. They proactively reached deep into the middle management layer to coach Senior Managers and Directors into future VPs at the company.
Come back next week to learn why you should be your own culture-demolition expert.
In other words, how to bring your existing team along as you hire new lieutenants while layering or managing out old ones.
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