The Distance Problem – Getting to Ground Truth

When you’re running a startup, you’ll rarely spend much time thinking about “ground truth.”   The truth of your company is in your face all day, every day.   You’re in the trenches full time.  You’re on every sales call.   You see every bug report in Slack. You know exactly why a deal slipped or why the latest deployment was three hours late.

But then, you hire managers.   As you grow, those managers hire managers.   Now the information you get is polished. It’s been filtered, aggregated, and, make no mistake, sanitized and spun.  Nuance, context, and tone have been removed, and your team will make every effort to let you know that, with any problem, “they’ve got it.”

I’ve seen this play out over and over and over again. I’ve got a green dashboard while the engineering team is actually burning out. I’m seeing a “strong pipeline” a month before we crater our numbers and half our reps quit. Those sales reps are struggling with a product gap they’ve been screaming about for months. I’ve never heard of it.

Scaling a B2B SaaS company isn’t just about adding headcount. It’s about building systems to ensure you remain safe as you scale. To lead effectively at scale, you need tools that provide visibility without devolving into micromanagement. You need to get back to the ground truth.

The Skip-Level

The most powerful tool in a senior leader’s arsenal is the skip-level meeting. This type of meeting is exactly what it sounds like. A manager’s manager meets directly with the individual contributors or front-line managers below them. I recommend a baseline of having these twice a year. If that feels like too much, start with once a year. The goal isn’t to audit your managers. It’s to understand what’s happening with their teams directly from their team members.

Why It Works

Skip-levels aren’t about “catching” your managers doing something wrong. They are all about signal and coaching. For signal, you’re looking across a broader scope of your company. You want to understand what, on a day-to-day basis, is working and what’s not. You are looking for patterns. If one person mentions a friction point in a process, it might be an outlier. If four people mention it, you have a systemic issue. Your middle management might be too close to it or too overwhelmed to report upward.

In coaching, it’s rare for a manager to be actively running a cover-up. Of course, bad actors exist, and actively covering up something is grounds for immediate termination. In the vast majority of cases, “missing” information is a byproduct of proximity. Your managers are going to be too close to the daily grind to see the patterns you can spot. This is a scenario where you, as a senior manager, are uniquely suited to coach them. You’re here to help and support. You’re not a hall monitor. You use skip-levels to gather raw data points. You use your experience to perform the issue analysis and provide context that they might have missed. This allows you to give highly detailed and concise advice. You can address the structural frictions they’re having trouble solving. You aren’t undermining their authority; you’re lending them your lens so they can see their own team’s reality more clearly.

The Ground Rules

To make these meetings effective, you have to be explicit about the “why.” If you just drop a calendar invite on a junior engineer’s plate, they’ll spend the next 48 hours wondering if they’re getting fired.

Make the purpose explicit

• Send them an email along with the meeting invite, telling them what’s up.
• Start the meeting by reiterating that.  “I’m here to listen and learn. I want to know what’s making your job harder and what’s making it easier. This meeting isn’t a performance review; it’s all about supporting you.   I’ll hear from you and your teammates and then use that to provide recommendations to your manager or the broader company on what we can do better.”

Strictly protect confidentiality

• If you take feedback from a skip-level and immediately run to their manager saying, “John said you’re a bad communicator,” you have permanently destroyed the trust required for this system to work.  It’s your job to figure out how to take all the information you get and make it impactful AND anonymous.
• Use a consistent question set: You want to be able to compare notes across the organization and people.  I recommend a really simple framework for that:
  • What’s working?
  • What’s not? 
  • What would you recommend we do about it?

A final note: it’s rare that you’ll actually need to come up with solutions for problems.   In my experience, your team not only knows what the problem is but what needs to be done about it.  The issue is that either they don’t have the authority to direct resources to make it happen, or they can’t turn the change into reality.   The simple rule of thumb here is that if you get two or more people on your team reporting (i) the same issue and (ii) the same fix, you should implement that fix without delay. 

The Ride-Along

In the old days, a ride-along meant literally sitting in a car with a sales rep. Today, it means sitting in on a Zoom call or a 1:1 with your team member.   For managers that report to you, I strongly recommend ride-alongs for their 1:1 meetings.   Senior leaders often shy away from this because they don’t want to “spook” or “micromanage” their team.   In practice, not doing this isn’t avoiding micromanaging; it’s avoiding management entirely.   If you never observe the actual work, your coaching becomes theoretical and increasingly less valuable.  You’re giving advice based on what people tell you they do, rather than what they actually do.

How to Do It Right

The key to a successful ride-along is the pre-brief. You must tell the manager whose meeting you are joining: “I am here as an observer and a coach for you. I want to see the quality of the interaction so I can help you grow.  This meeting is not a performance review; it’s about helping you develop.”

During the meeting, your job is to observe quietly.   Do not take over the call.  You can help by jumping in to save someone who is struggling and by modeling good behavior.   That noted, the bar for you jumping in should be high, and your presence should be as “invisible” as possible.

Coaching comes after the meetings, and you can share your feedback in two ways.   My personal favorite for 1:1 meetings is doing it live at the meeting with both the manager (who reports to me) and their direct reports.   That process has a ton of built-in accountability, and it stresses that productive management is a two-way street.   I almost always have practical observations for both parties, which hammer home that they both have work to do.   Obviously, if the meeting doesn’t work, the other option is to do it later, either as part of a 1:1 or as a standalone meeting.

For coaching, focus on the “how” and pay particular attention to interpersonal dynamics.   i.e., I’m not interested in addressing an issue that’s clearly one of the issues in the meeting.  My focus is on patterns of behavior that I want to see changed or addressed.   Accordingly, you’re also looking at process conformance and whether they’re following or not the basic rhythms of your business.

Office Hours

One final tool you can deploy to help address the distance problem is office hours.   Office hours are 30 to 60-minute slots every other week where anyone in the organization can drop in or book time with you to chat about whatever they like.   You’ll hear about friction points that are driving people up the wall that have zero chance of making their way to you through official channels.   If you can fix a small, annoying problem for a front-line employee, you’ve just bought a massive amount of internal capital.

No, You Aren’t Micromanaging

The most common reason people don’t take part in skip levels, or ride-alongs, is that they think it veers into micromanagement.  Is that a risk?  Sure.   In practice, though, 90% of the time you’re likely to undermanage rather than overmanage.   It’s your job as a manager to know what’s going on in your organization and provide intelligent, thoughtful guidance to your reports on how to address it.   Skip levels and ride-alongs are great tools to help in that.   

While the overwhelmingly likely scenario is under versus over manager, there are three rules or paradigms I’d recommend you keep in mind that’ll keep you well clear of micromanaging people:

• Do skip levels proactively, not just when things are on fire. If you only show up when there’s a problem, people will associate your presence with anxiety. Do them when things are going well, too.
• If you discover a problem in a skip-level, and you go directly to the team to fix it—bypassing their manager—you have just undermined that manager’s authority. Your job is to coach the manager to fix the problem, not to do it for them.
• If these check-ins become just “another meeting” without clear value or follow-up, the organization will eventually treat them as a chore to be endured rather than a resource to be used.   If you find a problem in them, you need to ensure it’s getting resolved by the right people in the organization.

Closing the Loop

The most dangerous feedback you’ll get from employees about skip-levels is something of the form: “I told my CEO what was wrong and they did nothing about it.”  If you ask for feedback and do nothing with it, you are better off not asking at all. You don’t have to fix every single thing that’s brought to your attention, but you must communicate what you heard as issues, which issues you’ll pursue fixing, and what you’ll do to fix them.

The Live Debrief Format

While you can do this via e-mail or Slack, my preference is to do a live debrief with the team.   That’s a pretty simple format:

• Thanks for your time meeting with me over the last few weeks
• Here are the common themes I heard as issues
  • I like using direct quotes here, as it gives the team a way to really see themselves in them
• Of those issues, here are the ones I’d recommend we fix and why
• Of the ones we’d fix, here’s the current plan on what we’re going to do

That transparency is what separates a “boss” from a “leader.” It shows the team that their challenges matter and we hear them.   It also gives you a chance to coach the team on core business realities: we have unlimited desires and finite resources.   Accordingly, here’s the set of stuff that it actually makes sense for us to work on. 

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