Progress Conversations Are Part of the Work

If you manage someone, a conversation about the progress is not just another thing you have to do.

At too many companies, talking about progress with people is seen as another “to-do.”

Something a manager needs to remember to fit in between customer issues, meetings, deadlines, email, and everything else that feels more urgent.

I understand how that happens. There is always more work than time.

But I think we create a problem when conversations about progress get treated as separate from the work itself.

Because if the work gets done through people, then talking with people about what they’re working on, what’s going well, what’s getting in the way, and what needs to happen next is part of the work.

And when those conversations don’t happen consistently, the consequences usually show up somewhere else.

Things like…

• A goal gets off track longer than it should.
• Someone keeps working on the wrong thing because nobody helped them reset the priority.
• A problem that could have been solved three weeks ago finally gets everyone’s attention because now it’s urgent.
• A capable employee waits too long for direction.
• A manager grows frustrated because they thought the expectation was clear.

Then everybody wonders why the work feels harder than it needs to.

I see this occurring in my coaching conversations all the time.

Sometimes a leader comes into a conversation focused on a problem that just surfaced, and as we talk through it, it becomes obvious that the problem didn’t start yesterday.

There were signs.
There were assumptions.
There were conversations that needed to happen earlier.
The issue simply became visible once the result was already off course.

That’s one of the reasons I believe regular conversations about progress matter so much.

Not because managers need to attend another meeting, but because those conversations create a place to notice something before it becomes expensive.

They create a place to clarify what matters now, compare expectations with reality, surface what is getting in the way, and make a decision while there is still time to do something about it.

And when those conversations are done well, they do something else too.

They develop people.

A good progress conversation isn’t the manager giving a status update or telling someone what to do next. It gives the other person room to think.

What are you seeing?
What’s going well?
Where are you stuck?
What decision needs to be made?
What are you going to do next?
What do you need from me?

That’s a coaching mindset.

And I think organizations get stronger when more leaders learn how to lead that way.

Execution at the organizational level is not just about having the right goals.

It is also about whether people are having the conversations that keep those goals alive.

I’ve worked with companies where the goals were clear on paper, but the conversations around them were inconsistent. People were busy. Managers cared. Everyone had good intentions.

But progress was being managed reactively.

That meant leaders spent too much time finding out what had already gone wrong instead of helping people move the right things forward while there was still time to influence the outcome.

The shift happens when talking about progress stops being viewed as something leaders have to remember to do and starts becoming part of how the company operates.

That changes the questions managers ask.
It changes when problems surface.
It changes how quickly priorities get corrected.
And over time, it changes how much ownership people are able to carry.

So here’s the question I’d challenge you to reflect on…

In your company, are conversations about progress part of how the work gets done, or are they something leaders try to fit in when they have time?

The answer probably tells you something about more than “having to do progress meetings.”

It tells you something about how your company executes.

— James

P.S. This is a big part of the work I do with individual leaders and leadership teams. If progress conversations are inconsistent, unclear, or happening too late, coaching can help leaders become more effective at turning those conversations into clearer expectations, stronger ownership, and better execution. Learn more about coaching.