One Way Even Great Sales Execs Fail: Not Spending Enough Time IRL With Their Team

Ask any seasoned VP of Sales what they’re short on, and you’ll get the same answer every time:
time. Time to forecast, time to recruit, time to sit with product, time to put out
customer fires. But there’s one place even great sales execs quietly steal time fromand it’s
the one place they can least afford to cut: real, in-person time with their team.

In the age of Zoom quotas and Slack novellas, it’s easy to convince yourself that you’re “with
the team” all day. Your calendar is full of pipeline reviews, your inbox is a CRM graveyard, and
you’re reacting to every red flag in real time. But if your reps rarely see you in the field, in
the office, or across the table from an actual customer, your leadership is happening at a
distanceand your revenue will eventually show it.

This is exactly the trap many otherwise excellent sales executives fall into. The dashboards
look healthy, the board is content, and the team is hitting “good enough.” Yet deal quality,
culture, and coaching quietly erode because the leader is managing through metrics instead of
managing through moments. Those moments almost always happen IRL.

Why Even Great Sales Execs Miss This IRL Piece

No one wakes up and says, “Today I will consciously avoid my sales team.” But modern revenue
leadership is built to pull you away from the front lines.

• Calendars reward meetings with other execs, not ride-alongs with reps.
• CRM and BI tools promise visibility, so you feel “plugged in” without
  leaving your desk.
• Distributed and remote teams make travel feel optional, not essential.
• Short-term metrics (like this quarter’s number) drown out longer-term
  investments like coaching, culture, and talent development.

The result? Even the best sales execs can spend 80–90% of their time in internal meetings,
forecasting sessions, and planning cycles while their reps are out in the wild, learning
lessons the leader never sees. When you only experience your team through dashboards and
slide decks, you stop understanding the texture of the work: the awkward handoffs, the
real objections, the subtle buying signals, the body language in the room.

The Hidden Cost of Not Being There In Person

On paper, everything looks fine. But the lack of IRL time shows up in ways that are maddeningly
subtle at first:

1. Coaching Becomes Theoretical Instead of Tactical

When you’re not regularly sitting in on calls or visits, your coaching becomes abstract. You
talk about “improving discovery” or “asking better closing questions,” but you haven’t watched
your reps actually do it. You’re coaching the idea of the deal, not the reality.

Effective coaching depends on specific, behavior-level feedback: “Let’s replay the first five
minutes of that meetingsee how you jumped into the demo before fully surfacing the pain?”
That kind of feedback is almost impossible if your only exposure to the deal is a one-line CRM
update and an optimistic forecast category.

2. Culture Turns Transactional

Sales is already a high-pressure, numbers-driven environment. Remove real human contact with
leadership and it quickly becomes transactional. Reps start to feel like “quota-carrying units”
instead of people you’re investing in.

In-person time builds the kind of trust that keeps top performers from answering recruiter
emails. When you show upon flights, in offices, in customer meetingsyou communicate, “Your
work matters enough for me to be here.” That lands very differently than a congratulatory Slack
message dropped between leadership offsites.

3. You Lose the Unfiltered Truth

People filter information up the chain. By the time a problem reaches the VP level, it’s been
softened, rationalized, or buried under PowerPoint. When you’re in the field or on the floor,
you get the unfiltered version: the offhand comment from a rep, the eye-roll in a team
meeting, the candid remark from a customer in the hallway.

Those unscripted moments often reveal more about your product, pricing, messaging, and team
health than any carefully curated QBR slide ever will.

IRL Time as a Strategic Sales Lever, Not a “Nice to Have”

Spending real-world time with your team is not a feel-good perk. It’s a strategic growth lever
for any sales organization, especially in SaaS where cycles are fast, products evolve quickly,
and customer expectations change monthly.

1. You See the Real Sales Process, Not the Idealized One

Your playbook might say you have a crisp, four-stage process with tight qualification and
rigorous follow-up. But when you join reps in the fieldor sit in person with them as they
run callsyou discover the messy human reality:

• Shortcuts taken under pressure to hit the monthly number.
• Workarounds for product gaps no one has documented.
• Customer objections that aren’t truly reflected in your “lost reason” picklist.
• Discovery questions that sound great in Notion but land awkwardly in real conversations.

Once you see how selling actually happens, you can refine your scripts, playbooks, and
enablement around reality instead of theory. That alignment alone can unlock serious gains in
win rate and cycle time.

2. You Turn Ride-Alongs into a Coaching Force Multiplier

A single day of structured ride-alongs or in-person call reviews can do more for performance
than a dozen generic training sessions. By sitting next to your reps, you can:

• Model the behavior you want to seehow to ask tough questions gracefully, how to handle
  silence, how to frame next steps.
• Spot subtle skill gaps: reps who oversell, reps who rush, reps who never confirm budget or
  authority.
• Give immediate, specific feedback while the conversation is still fresh.

Even better, these moments are highly memorable. Reps will remember “that meeting in Chicago
where you stepped in and re-framed the value prop” years longer than they’ll remember a
slide from your last sales kickoff.

3. You Build Cross-Functional Credibility

When you’re close to the field, you become a more effective advocate internally. You’re not
just saying, “We need this feature to close more deals.” You’re saying, “I watched three
customers this month struggle with this exact workflow. Here’s what they said. Here’s where
we lost them.”

That level of specificity earns you credibility with product, marketing, and finance. It
turns you from “the person who always wants more” into “the person who brings real customer
signal into the room.”

Designing an IRL Time Strategy That Actually Fits Your Calendar

The biggest pushback from sales execs is predictable: “I’d love to spend more time in the field,
but have you seen my calendar?” Fair. So don’t try to be everywhere. Instead, design a
deliberate IRL strategy that fits your role, team size, and stage.

1. Set a Minimum Weekly “In-Person Quota” for Yourself

Just like you expect your reps to hit an activity target, set one for your own in-person
leadership time. For example:

• Early-stage SaaS (0–10 reps): 2–3 days per week embedded with the team, on
  calls or in the field.
• Scaling stage (10–40 reps): 1–2 ride-along days per week plus in-person
  1:1s with your front-line managers.
• Later stage / global: A quarterly travel rhythm with regional tours, plus
  one standing “office day” per week where people know you’ll be around and available.

Put this time on your calendar first, then schedule everything else around it. If you don’t
protect it, it will disappear under an avalanche of “urgent” internal meetings.

2. Make IRL Time Structured, Not Random

Wandering around and high-fiving everyone like a motivational golden retriever is fun, but
it’s not a strategy. Treat your IRL time like any other crucial sales program:

• Decide which reps or regions you’ll focus on each month.
• Align your visits with key deals, renewals, or product launches.
• Set clear objectives: “I want to deeply understand how we’re selling into fintech,” or
  “I want to see three late-stage demos this week.”

Afterwards, debrief with your managers. What did you see? What surprised you? Which patterns
should shape training, enablement, or territory design?

3. Combine IRL Time with Modern Tools

In-person time doesn’t replace your tech stack; it makes it smarter. The goal is not to fly
around the country on vibes. It’s to pair qualitative insight with quantitative data:

• Use call recording and conversation intelligence platforms to pre-select deals worth
  joining live.
• Let CRM and revenue analytics point you toward segments where win rates are slipping or
  cycles are stretching.
• Follow up ride-alongs with short, written “play snippets” you can share with the whole team.

Over time, your in-person observations will feed back into better scripts, better training,
and more accurate forecasting. That’s the compounding effect you’re after.

Remote, Hybrid, Global: Does IRL Still Matter?

“But my team is fully remote,” you might say. “We’re globally distributed. IRL is a luxury.”
In 2020, that argument made sense. In 2025 and beyond, it’s more of an excuse.

You may not be able to see everyone every month. But you can:

• Anchor the year around 1–2 in-person sales kickoffs or regional meetups.
• Pair every trip to a major customer or conference with local rep meetings and ride-alongs.
• Rotate which regions or teams you visit each quarter so everyone gets facetime over the year.

Remote-friendly doesn’t have to mean relationship-light. In fact, distributed teams are often
more hungry for in-person leadership time, because digital communication can’t fully
replace the sense of alignment that comes from being in the same room, staring at the same
whiteboard, and arguing about the same pipeline.

How to Tell If You’re Not Spending Enough Time IRL

If you want a quick diagnostic, ask yourself a few uncomfortable questions:

• When was the last time I watched a rep run a full discovery meeting live?
• Could I accurately mimic how my top three reps open a call?
• Do I know the real, unfiltered objections customers are bringing up this month?
• Can my reps tell stories like, “Remember when you came out with me to visit that customer
  and we…?”

If the answers are mostly “I’m not sure” or “It’s been a while,” you’re leading at too much
distanceno matter how strong your numbers look today. And the painful truth of sales is that
today’s results are often a lagging indicator of yesterday’s habits.

Turning IRL Time into a Habit, Not a One-Off Fix

It’s tempting to read an article like this, schedule one big “field day,” and feel like you’ve
solved the problem. You haven’t. The real unlock is not a single intense week; it’s a consistent
rhythm.

Think in terms of cadence:

• Weekly: Block a non-negotiable window for in-person coaching, office hours,
  or ride-alongs (even if it’s just with reps in your home city).
• Monthly: Do a deeper-dive visit with a specific segment, vertical, or
  region.
• Quarterly: Run or attend in-person sessions where you bring the team
  together to align on strategy, messaging, and priorities.

Over six to twelve months, this cadence compounds. You’ll spot patterns earlier, adjust faster,
and develop a much sharper intuition about what’s really happening in your funnel.

of Hard-Won Experience: What IRL Time Actually Feels Like

Let’s get practical and a little bit personal. What does “spend more time IRL with your team”
actually look like when your calendar already resembles a Tetris board on hard mode?

The Founder-Led Sales Stage: “I Don’t Have Time for My Own Flights”

At an early-stage SaaS startup, the founder/VP of Sales combo is living on airplanes and
lattes. The temptation here is to treat reps as an extension of your calendar: “You handle the
smaller accounts while I chase the whales.” But the fastest-growing teams do the opposite.

One founder I worked with made a rule: for the first year after hiring their first three reps,
they joined at least one call per week per repeither virtually with cameras on or in person if
the deal was big enough to justify travel. It was exhausting. It also meant that within six
months, their reps sold almost exactly like the founder, which led to consistent, repeatable
deals. By the time they scaled to ten reps, the team had a shared “sales language” forged in
real meetings, not Notion docs.

The Growth-Stage VP: “I Live in Forecast Meetings Now”

At the growth stage, things get trickier. You inherit managers, territories, and a board that
wants clarity on everything. One VP I know looked up after a quarter and realized they’d spent
more hours building slide decks about deals than actually attending them.

They made a simple but radical change: every week, they canceled one internal meeting and added
a “Field Friday.” That meant either traveling to a key region once a month or dedicating the
day to being physically in the officeno Zoom, no slides, just time with reps and managers.
They joined discovery calls from conference rooms, sat in on renewal negotiations, and held
impromptu coaching sessions at whiteboards.

Within two quarters, two big things happened: win rates on late-stage deals ticked up, and
attrition among mid-performing reps dropped. Why? Those reps finally felt seen. They had direct
access to leadership, real-time feedback, and support when deals got weird (and they always
get weird).

The Global Org: “There’s Always Someone Asleep”

In larger, global organizations, the problem isn’t desire; it’s physics. You simply can’t be
everywhere. A CRO I spoke with adopted a tour-based model: each quarter, they picked one region
to focus on. For that region, they committed to:

• At least one multi-day in-person visit.
• A dinner with the top performers and emerging talent.
• Live reviews of two or three strategic deals.

They treated these tours almost like mini-conferencespacked agendas, lots of listening, and a
clear follow-up plan. Reps in those regions described the visits as “worth six months of Zoom
calls.” They felt heard, got better direction, and built a personal relationship with someone
they’d previously only seen in all-hands meetings.

The CRO didn’t stop using digital tools. They still relied heavily on call recordings, CRM
reports, and revenue analytics. But the combination of those tools with intentional IRL time
gave them something they hadn’t had in years: real confidence that what they saw in the
dashboards actually matched what was happening with customers.

That’s the heart of this whole topic. IRL time isn’t about nostalgia for office life or
racking up airline miles. It’s about collapsing the distance between the story you tell the
board and the story your reps live every day. When those stories matchbecause you’ve been
there to see ityou lead better, coach better, and sell better.

Conclusion: Leadership Doesn’t Scale If You Don’t Show Up

The irony of sales leadership is that the more you scale, the more you’re tempted to retreat
into slides, spreadsheets, and strategy docs. But revenue is still created one conversation at
a time, between a rep and a buyer, in the messy real world. If you’re not spending enough of
your time thereIRL with your teamthen yes, even as a great sales exec, you’re quietly
failing at one of the most important parts of your job.

The fix isn’t complicated, but it is intentional: protect in-person time like you protect
board meetings, treat it as a strategic lever instead of an afterthought, and build a cadence
that makes presence a habit rather than a heroic exception. Do that consistently, and you
won’t just close more dealsyou’ll build a sales org that people actually want to be part of.