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Chapter 10: New Manager’s Playbook–Having Difficult Conversations With Employees

It’s a fairly routine deployment, but this time, it’s not full of victories. Something goes wrong—seriously wrong—and when the dust settles, you discover the problem centers on a basic mistake from one of your programmers.

To add to the pain, this particular programmer just happened to leave work early that day and miss all of the fun.

Your stomach is churning, your head is pounding, and you’re about ready to rip loose a torrent of frustration on innocent bystanders.

Welcome to management! Now is the perfect time to have a difficult conversation.

Difficult Conversations, Defined

A difficult conversion is any interaction you have with your team members that puts you in position of delivering feedback or correction.

As a programmer, you probably weren’t forced to face this situation because you were responsible for your own work, period. As an agency owner who’s now managing an entire team, you’ll be faced with initiating these emotionally-charged exchanges on a regular basis in a supportive, professional manner.

Difficult conversations can range from pointing out a flaw in a piece of work, reinforcing company policy, or the ultimate—having to tell someone to clean out their desk and pick up their last paycheck on the way out the door.

We all love giving positive feedback, like breaking the news about a promotion or heaping praise on the person who saved the project with an elegant workaround.

But when someone you manage screws up and it’s time for some good old-fashioned accountability, most people would rather pay out of pocket to endure a root canal than have to tell a coworker that they screwed up.

Why Difficult Conversations Are… Difficult

Let me point out the obvious. No one likes conflict.

In today’s work environment, where we’ve been steeped in politically correct notions of self-esteem and egalitarian relationships, these top-down conversations feel soooo 1970s.

Rather than playing the nice guy, you have to act like an authority figure, asking people to toe the line, straighten up, and start doing better work. You’re afraid of coming off like your junior high principal with his polyester suits, rigid ideals, and wooden paddle.

Warning: Duck and Cover is a Dead End

Naturally, most people avoid that uncomfortable place.

The problem is that most managers haven’t found a more functional system. When it comes to team issues, they’d rather sit around singing “Kum Ba Yah” than give negative feedback.

In fact, most well-intentioned new managers I meet tend to fall into one of two less-than-productive camps when it comes to conflict.

  • Those in the first camp don’t talk about problems at all, hoping deep in their hearts that things will magically improve and that everyone will just do everything perfectly so they won’t have to step in at all.
  • Those in the second camp don’t think they should have to give correction and instruction—team members should just “get it”. Usually, after months of watching a programmer make mistake after mistake (without intervention), their internal scorecard gets filled up, and they decide that this person just doesn’t cut it. They seethe with frustration and decide that the only solution is to fire the guy.

Clearly, there’s a lot of room between those two positions for clear, helpful communication, even if it’s not easy.

So what’s the answer?

Have More Difficult Conversations

Don’t start looking for a magical mantra or a perfect script to make these uncomfortable situations vanish. You want to learn to steer the ship, not look for an escape hatch.

A willingness to look this problem in the eye and practice having tough conversations pays huge dividends. Believe it or not, these conversations can be handled in a way where you and your team can see them as a normal—and productive—part of the design process.

These tricky conversations can actually be an effective tool to connect with team members, invest in their skills, and help the company deliver a quality product that keeps them economically viable.

Before you pull someone aside for a difficult conversation, it can take the pressure off a bit when you know your role and own it in these situations.

Be the Conductor

Let’s go back to our analogy of the technology owner-manager as the conductor of an orchestra.

Up at the podium, the conductor has the perspective to see and hear everything. They know when the bassoon player misses her entrance. They hear the sloppy fingering of the third violins in a difficult passage.

What does the conductor do in response?

A skilled conductor will stop the rehearsal, gently and clearly point out the mistake, and have the musicians run the section again, several times if necessary.

Conductors know there should be little or no shame in these exchanges—it’s just part of preparing an entire group for a magnificent performance. Usually, a few minutes of focus can smooth out the problem.

While the musicians never enjoy getting singled out for less-than-stellar playing, they also understand that this attention lands on everyone eventually. It’s part of being in an ensemble.

For more persistent problems, conductors will meet individually with the musicians and suggest something like extra rehearsal time or one-on-one sessions with the section leader. If that intervention doesn’t do the trick, then it is very possible that they’ll be looking for another bassoon player next season.

In other words, clear communication concerning individual and team performance has a predictable pattern, and the world doesn’t fall apart every time the conductor points out a need for improvement.

Small conversations, big payoff

Likewise, you can offer ongoing feedback in small, granular ways so you grow comfortable giving correction and your team doesn’t panic when they receive it.

One easy way to do this is by offering a bit of criticism every time you review a piece of work from a team member, even (and especially!) if it’s minor. Your programmers will soon understand that you’re paying attention, and the nudge will help them level up their game.

For the naysayers who think that their team should just “get it” without even this simple level of intervention, let me give you a wake-up call.

Yes, we’ve all had employees who walked on the scene somehow knowing exactly what needed to be done and did it without a whisper of direction. It is a beautiful thing to behold.

After dealing with both interns and seasoned programmers for years, I can tell you that these rock stars who seem to automatically “get it” had someone invest in them and train them in the basics of team culture.

Now it’s your turn. Here’s how to use that power wisely.

Be a Surgeon, Not a Barbarian

In every manager’s office there hangs an imaginary sword.

It’s a sword of decision and power that was handed to you with the position, making it possible for you to respond to your team’s needs without having to run to your manager every time there’s an issue.

Most new managers eye it nervously, hoping and praying that they’ll never have to touch it. Others are more passive-aggressive, eyeing it in front of team members and saying, “Don’t make me reach for this.”

In either case, the sword rarely gets used, which just makes the manager look really clumsy every time he tries to pick it up.

Practice creates ease and finesse

Watch little kids playing with swords. The first time they have one in their hands, they either make feeble jabs or they run around screaming and hacking the air… and their siblings.

New managers, unfortunately, do the same. Some are so timid with their power that their team has zero confidence in their skills or leadership abilities. Others use it only when they’re boiling over with frustration, leaving their team to hit the decks to avoid their wrath.

When managers make a conscious choice to practice using this power on a consistent basis with an average workflow, they’re reducing their learning curve and increasing their effectiveness.

With a little practice, you can turn your sword into a scalpel, making small, pinpoint cuts that leave little mess and quick healing, just as a surgeon does.

The keys to this approach are a commitment to improving a bit each week and having a simple, reliable plan to follow. After years of trial and error and watching some truly remarkable managers, here’s the playbook I’ve created.

Six Steps to Navigating Difficult Conversations

Whether your first difficult conversation is in the future or you’ve been handling them badly for months, have the courage to go through the process whenever it presents itself. I guarantee you, in most cases, the outcome won’t be as bad as you think it will be.

Step 1: Notice the signals that say, “Time for a difficult conversation!”

When you’re having conflict with someone, you can feel the frustration all over in your body. Pay attention to the pit in your stomach, clenched fists, or tension headache. They’re a signal that it’s time to clear the air.

Sometimes, the signal isn’t a feeling. You might hear yourself say things like:

This always happens…
He never gets this right…
Not again…

Whatever your particular trigger, know it well and use it as a flag to take action instead of bury your head in the sand.

Step 2: Don’t fume. Commit to take constructive action.

Avoiding action will only create resentment. Choose a time in the immediate future where you can discuss the problem with this person so you can both move forward.

Step 3: Make a plan.

If you’re on the verge of losing your temper, go for a walk or take some deep breaths. This is not a time to prepare an exact script or build a bullet-point litany against this person, it’s just time to zero in on the core of the problem and possible solutions.

Let off a little steam, talk out loud to yourself (in private!) or sketch out your opening line (see below), but don’t burn a lot of time on this point. Move forward.

Step 4: Have the meeting in private—soon.

Yes, this is uncomfortable for the team member, but talking to them one on one will provide a calm environment, remove the possibility of distractions, and keep eavesdroppers out of earshot.

And if they do have that sinking feeling as they follow you to a private room for a conference, that’s okay. It’s an honest, nearly unavoidable reaction. This is a matter that needs attention, and they will know that immediately.

Step 5: Be steady and on point.

This is not the time to pull out every infraction from the past six months or be so vague about the problem that your team member has no idea what problem you’re actually discussing.

Don’t yell. Don’t repeat yourself. Don’t bombard them with information in the hopes of making your criticism more valid.

Venting your anger isn’t productive, so stay focused on the outcome you really want from the discussion. Using a single framing sentence usually makes things crystal clear.

I like to use the word “disappointed” in these discussions. It’s a subtle way of telling this person that I do hold them in high esteem, and this incident doesn’t match that overall impression.

Here’s one of my favorite go-to scripts in these tense situations:

John, I was really disappointed when X happened. I want to understand why and find out what we can do to make sure it doesn’t happen again.

Step 6: Shut up. Listen. Then listen some more.

Silence can be a very powerful tool in these situations. While it can be excruciating to let empty space hang out there, do it.

Drink some coffee or count to 10, but let the other person have some time to collect their thoughts or get past an emotional moment.

When your team member does respond, resist the temptation to refute what they’re saying or meet their defensiveness (which is completely understandable) with defensiveness of your own. Be willing to take the blame for any mistakes on your part and circle around to the solution.

Always focus on the solution.

While anticipating these difficult conversations is never a picnic, each time you move past the fear and choose to get through them, you develop more experience, more perspective, and more confidence.

Even better, you are able to improve communication within your team, making your job even easier.

One day, you may even find a team member at your desk saying,

Can we talk? I screwed up and I want to make sure it doesn’t happen again.


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