Most of what I know about doing this job well, I learned by getting it wrong first. This is the working list I wish someone had handed me twenty years ago, not in order, not a highlight reel.
In this article
- Preparation isn’t optional, even when you think you’ve done enough
- Managing up is a skill, not a compromise
- Letting someone go too slowly is not the kind option
- Big rocks first, or your calendar fills with sand
- Coaching isn’t one playbook for every person on the team
- Credibility can be built before you ever meet someone
- Adaptability beats the plan you showed up with
- Hypergrowth burns people out quietly, and it’s the leader’s job to see it
Key takeaways
- Waiting to let someone go doesn’t protect them, it protects you from a hard conversation
- A rocks-first calendar beats a reactive one every single week
- Coaching without diagnosing motivation and aptitude first is generic advice on a schedule
- Content built trust with a prospect before I’d ever said a word to them
- A headquarters playbook doesn’t scale down, it has to be rebuilt for the market
Preparation isn’t optional, even when you think you’ve done enough
My first real interview was for an internship. This was early enough in the internet’s life that search engines were unreliable and half of everything wasn’t online yet.
I tried to find the company’s website. Couldn’t find it. So I assumed they didn’t have one, and walked in without having read a single thing about them.
They had a website. I just hadn’t found it.
I showed up with nothing. No sense of what they did, who their clients were, why I might be a fit. It was obvious within five minutes, and it was mine to own.
Since then, I’ve never walked into a room without knowing:
- Who I’m meeting and what they’re actually accountable for
- What the company has said publicly in the last twelve months
- What I’d ask if I were sitting on the other side of the table
- One thing I could bring that they didn’t ask for
Preparation isn’t a competitive advantage. It’s the floor. Skipping it doesn’t save time, it gambles with a first impression, and first impressions in B2B are expensive to fix.
Managing up is a skill, not a compromise
Nobody teaches this one directly, so most people learn it by accident or not at all.
Managing up isn’t playing politics. It’s understanding what your manager is personally accountable for, and making that easier for them to deliver, the same discipline that closes a deal with a buyer.
I’ve watched good salespeople struggle for years because they treated their manager as an audience instead of a stakeholder. The moment you start managing up, the job gets easier, not because you’re doing less, but because you stop fighting the person who controls your resources.
Letting someone go too slowly is not the kind option
Jeff Weiner, LinkedIn’s CEO through most of my time there, repeated one line so often it became part of the culture: not addressing an underperformer fast enough isn’t kindness, it’s unfair to everyone.
Unfair to the organization, because the gap doesn’t close itself. Unfair to the team, who is quietly covering for it. Unfair to the person, who deserves to know clearly and early rather than watch their own manager avoid the conversation for two more quarters.
I’ve felt the pull of this from the other side of the table. Wanting to give someone one more chance, one more quarter, because the conversation is uncomfortable and the alternative feels harsh. It rarely is.
The kind thing and the fast thing are usually the same thing. Most leaders wait because the delay protects them, not the person.
Big rocks first, or your calendar fills with sand
Mike Gamson, who ran LinkedIn’s global sales organization, used the rocks-pebbles-sand idea constantly. Big rocks in the jar first, the priorities that actually matter. Then the pebbles. Then the sand fills whatever’s left.
Do it backwards and the big rocks never fit. Simple to say, hard to protect.
The sand, the emails, the pings, the small fires, is loud and immediate. The rocks, the account plan, the hire you’ve been putting off, the pipeline review that actually matters, can wait one more day. Until they can’t.
The test I still use: before the week starts, name the two or three things that have to happen no matter what. Everything else is negotiable.
Coaching isn’t one playbook for every person on the team
The situational matrix I use as a manager plots two things: how motivated someone is, and how capable they are at the task in front of them. High motivation and low skill needs something completely different from high skill and low motivation. Treat them the same and you lose both.
| Motivation | Aptitude | What they need |
|---|---|---|
| High | Low | Coach and build the skill fast, their energy carries them through the learning curve |
| High | High | Stretch them, delegate ownership, not tasks |
| Low | High | Find out why, usually a trust or belief problem, not a skill one |
| Low | Low | The hardest conversation, and often a fit problem, not a fixable one |
The GROW coaching framework, goal, reality, options, will, sits alongside this well once you’ve worked out which box someone’s in. Skip the diagnosis and even a good coaching model becomes generic advice delivered on schedule.
Credibility can be built before you ever meet someone
Before I ever worked at LinkedIn myself, back when I was still in a regular sales role, a prospect walked into our first face-to-face meeting and thanked me. Not for a proposal. For something I’d posted on LinkedIn that had actually helped him.
We hadn’t spoken before that meeting. I hadn’t pitched anything. The trust I needed to close that deal had already been built before I walked in the room.
That’s the part most advice about LinkedIn misses. It’s not about reach or likes. It’s about being useful to someone before you need anything from them, so that by the time you do ask, you’re not a stranger with a pitch.
The best thing LinkedIn ever did for my sales career happened before a single meeting was booked.
Adaptability beats the plan you showed up with
In 2012 I moved to Dubai as one of three people on LinkedIn’s Middle East founding team. No local brand recognition. No regional playbook. And a market where relationships drove buying decisions in a way the headquarters sales motion hadn’t accounted for at all.
The plan we arrived with didn’t survive contact with the market. Relationship first, use case second, procurement third, that was the actual sequence, and it was the opposite of how the same motion worked in Europe.
You can’t scale down a headquarters playbook and call it localization. I’ve seen companies try this in the GCC for years since, arriving with a distribution plan and no positioning work, wondering why the home-market cycle doesn’t apply.
Hypergrowth burns people out quietly, and it’s the leader’s job to see it
I’ve spent a lot of my career inside hyper-growth environments, and one pattern repeats. The people most passionate about the work are usually the ones it drains fastest, because passion doesn’t come with a natural stopping point.
Balance treats work and life like two things competing for the same hours. Harmony runs them side by side, so neither one quietly eats the other.
I’ve watched the cost show up in relationships and in families before it ever showed up in an attrition number. By the time it hits the numbers, it’s already been happening for a while.
- Notice who’s always the first reply and the last one online, that’s not always dedication
- Ask what someone gave up this quarter, not just what they delivered
- Model the boundary yourself, a team copies what a leader does, not what they say
