Hard Conversations

Hard Conversations

Justin Nearing

I failed an interview last week.

I don’t like to think of interviews as pass/fails. Most of the time having a company decide not to go forward is not a failure. It’s just misalignment.

But in this case, it was a failure, because the feedback indicated the interviewer had taken a negative impression to something I thought wholly positive.

It was an example on the skill of having hard conversations.

Looking back, perhaps I shouldn’t have used the most difficult conversation I’ve had in my career as the example.

It was a time I had taken a particularly tactless and brutish approach.

So I am SHOCKED the takeaway my interviewer received was I was tactless and brutish.

Hard Problems, Hard Conversations

The example I had given was a “wheels-about-to-come-off” moment unless we did some “cowboy shit.”

Both of those are technical terms.

That’s not so bad in itself, except we had to do this across the company.

In essence, our Technical Debt went to Collections (still writing that article).

I was on point to navigate us through. In this case, kicking and screaming.

Things became difficult when we started discussing this with the team managing the most critical service in the company.

That team did not do cowboy shit.

Furthermore, there was a steep power imbalance between our team and the team I was upsetting.

Our job was to support them, help keep their wheels turning, and it had long been our priority to drop everything to help the VIP team.

Buuut the wheels were literally about to come off. Right now.

Which meant this was also their problem. Right now.

This is the setup for a hard conversation.

An Underrated Skill, Learned the Hard Way

Hard conversations usually boil down to having to break incorrect assumptions:

  • A junior whose gung-ho about being a senior, but still struggles with the ownership of the tasks they currently have.
  • Upsetting a previously made decision/timeline/etc. because you have context previously unconsidered.
  • Some product/service not worth the amount being charged.

The list goes on, but you get the picture.

Hard conversations often boil down to assumptions inconsistent with the facts on the ground.

And as hard as that is, its harder still to have that conversation tactfully.

The conversation I was having with the VIP team was not done tactfully.

In retrospect, I don’t think there was a tactful approach.

The politics, the timelines, the incentives were all conflicting.

At the critical moment somebody needed to be the bad guy in the room, cut through the shit, and move things forward.

I’m that guy.

Crafting Narratives Is Hard

This was one of the most pivotal moments in my career, to me it’s the literal moment I “became” a Lead.

Being forced to stand up to someone, feeling the uncomfortable feelings that comes along with hard conversations-

It’s a requirement to being a Lead.

And yet the way I communicated this gave the complete opposite impression.

The way I framed it was that I was tactless and brutish, and more importantly that I didn’t have the introspective ability to understand that.

To an interviewer, it’s easy to extrapolate that into thinking I have a pattern of bullying behavior.

The irony is I'm introspective to a fault.

The reason this story is so important to me is because I was so uncharacteristically direct.

And honestly, the relationship between our teams drastically improved after we got through the hard part.

The wheels were replaced, with a new system allowing both teams to deploy changes safely and independently.

And it forced our teams to start communicating regularly, so feedback loops became much faster.

It’s just that it required some tough conversations to get us there.

The point is crafting effective, efficient narratives is a tough skill to master.

Aaaand I messed it up this time.

I ain’t shook about it.

I had about a minute to deliver all this in an interview setting- Interviews themselves being the iconic hard conversation.

Lessons Learned

Since then, I’ve put a lot more effort into injecting tactfulness into hard conversations. There’s a bunch of strategies here:

  • Sit the person down and lay out all the information, decide together what the right decision is.
  • Get someone who outranks the both of you and provide them all the context.

But really,

The best approach is to avoid needing hard conversations in the first place.

If a hard conversation is boiling down to bad assumptions, dispelling those assumptions early and often means many easy conversations instead of big hard ones.

It’s those load-bearing assumptions that break things.

  • Frequent feedback prevents bad assumptions.
  • Forging trusting relationships allows for critical feedback.

During that crisis, I felt I ain’t got time for that. Cracked eggs for messy omelettes was on the menu.

The whole thing was a mess, and I feel bad that I wasn’t able to craft it into a better 30-second anecdote in a interview.

But writing about it provides some catharsis, and the next interview I’ll be that much better telling this story.

Damn I’ll probably send them a link to this article.