How to dig into a problem

Posted by kdow on Feb 24, 2016 10:45:06 AM

Digging in. Creatively.

Now that I’m managing a bunch of people, often in remote locations, I need to develop some new skills of my own. I’ve been receiving mentorship from some VPs & MDs in the company I work for. And some of these experiences have been remarkable for my personal development.

Everyone in a leadership role waxes lyrical about the dreaded 1:1. Their prose is typically very different to that of those receiving the 1:1. A meaningful catch-up (which is what I title 1:1’s) is not your time as a manager. It’s the recipient’s time to air issues, get advice or just get some face time.

As a leader, the worst thing you could spend that personal time doing is trying to berate someone for mistakes or try to solve big, specific & complex issues. That’s not what this time is good for. And doing anything other than listening and sharing advice can turn into a session involving talking at someone. Instead, the most valuable thing you could do as a leader is give coaching advice and try to steer the conversation in such a way that the person receiving the 1:1 comes to their own realisations about what behaviours they could work on.

And the way to do this is to be a small child.

Small children are great at digging into problems, data sets or information.

Small children dig into problems in a conversational routine that resembles this:

“Are we going to x?”

“When will we be there?”

“Why are we going?”

“Why will it take that long?”


In the back of a car that would drive any parent mad. But think about the information in the purest sense. This line of irritating question can deliver some pretty nuanced information. Yes, you’re going to some location & it’ll take some amount of time to get there. The reason you’re going to this location is some reason and it’ll take that long to get there because something. And why. Why is any of this happening?

Let’s create a demo scenario. The problem we’re trying to solve as a leader is that a colleage has created a weird solution to a simple problem. They have not articulated well to you or themselves. The issue is that they have a very insular way of communicating to their colleagues, who rely on them. Instead of walking over to them and chatting, they built a communication tool with code.

In their mind, they solved the problem. Their colleagues can schedule time and communicate with the individual through this little app. But to their colleagues, there’s an odd tool that now needs to be used when trying to communicate basic information or request time with this individual. It feels jarring and useless. “Why do we have to adopt this tool?!”

As a leader, your job is to make them realise this without calling it out. Making them realise that there’s a better way to achieve this & coaching through the problem, rather than creating conflict that may damage a relationship.

So, be a kid!

Let’s take that as an example, being a kid to tease out the issue.

Q: “What problem is your app idea solving?”

A: “I get good information to answer questions from my colleagues before they book time in my calendar.”

Q: “Cool. So before this app, what was the process?”

A: “Well, we spoke in-person in the office but I never got good information before my colleagues booked my calendar.”

Q: “Interesting. So, what problem is your app idea solving?”

Okay, so let’s pause our conversation. We’ve now passed enough time in your little conversation to be able to ask the same question. Your smart, brilliant colleague knows that this has happened. Anyone who’s done any management before probably knows why and will answer you pretty directly to justify their decision. But for the most part, your colleague will shift their answer a bit.

A: “Well, it makes a formal process to schedule time with me. It gives me more time to work on things without the wasted time talking to colleagues idly.”

Q: “Interesting. Do you think before the app existed you just hadn’t set decent expectations with your colleagues?”

A: “Maybe. I think it was clear what I wanted.”

Q: “But do you think it was actually clear what was expected from your colleagues?”

A: “In some cases, maybe not.”

Q: “Interesting! So, what problem does the app idea solve?”

Let’s pause again. We’ve now hit on the root problem of what’s going on. Expectation versus reality in our demo scenario. Our 1:1 recipient is now thinking on their feet about what it is that they could do better day-to-day, and that culturally having an app to communicate isn’t nearly as effective as having a chat; even if that chat is over Slack.

Some people will still defend their position, and that’s fine. It might take a few sessions to tease out the problem and ultimately solve it in a good manner. But doing it in a gentle session where all you’re doing, as a manager, is digging into a problem and letting your colleague solve it themselves is far better in the long run.

Let’s say you didn’t dig in. Let’s say you didn’t take an inquisitive approach over time. Let’s say you railroaded the conversation by saying this app idea sucks, is jarring and doesn’t necessarily give your colleague good information. Then you’re hitting them where it hurts: in their solution to this specific problem. Which means they’re less likely to come up with creative solutions to new issues in the future. Even worse, they’ll just come to you to solve every issue they have; which is not why you hired smart, creative people. Moreover, they’ll hate your 1:1 sessions and not derive any real value from them. And they’ll approach everything they do — for a while anyway — with some level of trepidation for fear or reproach or fearing for their jobs (because the more junior you are, the more you fear your job will just be ripped out from under you).

And that’s why digging in is so important. It’s nicer, more useful and over time embraces an approach that encourages entrepreneurial thinking, creativity and everything in-between. There’s now pithy one-liner to end this post, but that’s because I spent a lot of time digging into what I was trying to say. The point here being that digging in takes time. Digging in is hard, and digging in is really valuable to everyone.