One of my favorite phrases I borrowed from the London Underground - “Mind the Gap” - has become a powerful metaphor in my leadership coaching and advisory work. Why? Because most conflict, disappointment, and underperformance stems from a typical root cause…
A GAP BETWEEN EXPECTED OUTCOMES AND THE CURRENT REALITY
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Whether you’re building a team, scaling systems, or fixing a broken GTM motion, the 3 questions I consistently ask of myself and my team are:
Have we clearly defined and documented the expected outcome?
How big is the gap?
How do we close it?
Here are three critical operational areas - hiring, technical systems, and team execution:
1. Hiring for Gaps: Capability + Behavior Scorecarding
Hiring isn’t just about checking boxes. It’s about solving for specific gaps your team or other departments in the company currently face.
I’m a firm believer of using scorecards for hiring for these gaps. The interview scorecards I’ve personally built typically focus on only two key lenses - ”Capabilities” and “Behaviors”.
Capability Gaps — Can this person do what we need them to do?
Behavior Gaps — Will this person show up the way we need them to?
Here’s how I recommend addressing both:
Step 1: Build a Capability Scorecard
What are the required outcomes this hire needs to deliver? List out the 5–7 desired capabilities this hire must have to deliver the role’s desired outcomes in the next 12–18 months. Then create a list of interview questions based on capabilities required to deliver those outcomes. Write down the capabilities as the interviewee answers your well designed questions. Now produce a 1-5 score (or 1-10) of the strength of the capability you believe your interviewee has against that capability.
Example: Hiring your first FP&A lead at Series B? You might score them on the…
Building driver-based forecasts from scratch
Running board-ready scenario models
Partnering cross-functionally with GTM or product leads
Behavioral Interview Scorecards
For behaviors, I use a similar framework to the capabilities scorecard I just described. Some of my favorite key behaviors?
Ownership: Do they take initiative or wait for instruction?
Adaptability: Can they flex with startup ambiguity or changing priorities?
Humility & Collaboration: Will they build trust across functions?
Cook’s PlayBook tip: What are your team’s and/or your company’s “1st Principle” cultural values? What behaviors are required that demonstrate these values? Now develop a list of interview questions that surface “How” an interview tackled some of their hardest problems or adversity they faced in their current and past companies. Don’t forget “Behaviors” are the way that people get shit done. How they do what they do. Not the what. Not the result. Now score behaviors against your cultural gaps.
If your team lacks speed, hire for urgency. If your exec team lacks the ability to effectively challenge each other, hire a more direct truth teller as your next exec.
2. Solving Technical Gaps: From Bandaids to Bridges
I see this mistake a lot: A team diagnoses a technical symptom (e.g., forecasting is slow, dashboards are wrong), then buys a shiny tool without solving the underlying capability gap.
Here’s the fix: use a Capability → System mapping exercise.
Example: Fixing the Forecasting Stack
Let’s say your revenue forecast is consistently off. What’s the actual gap?
Is it data integrity? (Then you need better source systems and data hygiene)
Is it model design or data speed? (Then focus on new processes that increase speed to data and/or building better APIs for various sub-systems to talk to each other)
Is it governance and accountability? (Then you need to design better decision rights, cross checks, and inter-department collaboration)
So before you jump into any one of these fixes, clarify the gaps and prioritize them. From there, it’s typically an upgraded system, upgraded personnel, or re-architected operational processes.
People - Systems - Processes
Most times, it’s a combination of more than 1 of these problems. The prioritization of the sequencing of the potential “fixes” matter.
3. Sales & GTM Gaps: Diagnose the Entire Sales Funnel and Customer Journey… Not Just the Team or Personnel.
Hiring a new VP of Sales won’t fix a broken GTM engine. Too often, I see Founders and CFOs fire the sales leader when the real issue lies in one of three places:
Poor ICP (Ideal Customer Profile) definition or customer segmentation targeting
Lack of sales personnel ownership
Actual product readiness
Mismatch between marketing and sales metrics. What marketing thinks is a “qualified lead” is not aligned with what sales thinks is a qualified lead.
A few “Mind the Gap” Questions for GTM:
Are lead quality and lead conversion aligned? If not, then there’s a targeting gap.
Is your sales process repeatable or tribal knowledge?
How good are the sales personnel handoffs to each other? From SDR (Sales Dev Rep) to Sales Coordinator to Account Executive to Customer Onboarding team.
Is there a process gap somewhere in these touchpoints?
What are our top 3 customer pain points this week?
What is our biggest customer objection to not buying this week?
Are customer win/loss reasons documented and shared? Do you even interview your customers after key wins AND losses? If not, you’re flying blind.
Fixing the GTM gap starts by mapping out each part of the buyer journey and you guessed it… SCORING IT!
Transparency wins. Making these gaps visible is over half the battle. Transparency can become your new cultural currency.
These are such relatively simple concepts but I don’t see very many teams actually taking the time to WRITE IT DOWN and COMMUNICATE IT. But they sure can verbalize and “intuit” the problem correctly when I probe with my own powerful questions.
Cook’s PlayBook Tip: Develop Sales and Customer Journey Scorecards across Marketing, SDRs, AEs, and Customer Success. Score each GTM motion from 1–5 and compare to benchmarks.
KEY LEADERSHIP TAKEAWAY:
Conflict isn’t the problem. The gap between expectations and reality is the problem.
Not addressing this gap properly is what creates conflict, dysfunction, underperformance, and misaligned priorities.
Next time you feel any one of these typical operational issues (conflict, dysfunction, lack of focus) ask yourself, “What’s the gap in your own expectation?”
Before you start jumping into fix, ask, “Is it truly a people problem? Or is it a systems problem? Or is it an ownership/process problem?”
Write down your expectations, your gaps, and your scores. Communicate them to your team and see if there is alignment or misalignment with their expectations and their respective gaps.
Think about normalizing new leadership language and key phrases inside your company such as:
“Where’s the expectation-reality gap right now”?
Teach your leaders to use this language proactively not reactively. This slight shift in questioning shifts the tone from post-mortem blame/judgement to shared expectations and joint problem-solving.
Is there misalignment in your expectations vs “theirs”?
Then I recommend running more “pre-mortems” vs simply “post-mortems”.
Example Pre-Mortem Questions:
How do we define success of our upcoming product launch? (PS. Write down the answers and publish them before you launch).
What are the assumptions in our next GTM campaign?
Bottom Line:
Only after you define gaps and then prioritize gaps can you start closing gaps efficiently. You ensure gaps stay closed with the proper capabilities and behaviors aligned to desired future outcomes (a.k.a - “Expectations”).
That’s how you turn “Mind the Gap” into your go-to leadership operating system.
Want more stuff like this?
All the Best Ofs,
Jim
