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How to run world class One to Ones - Part 2: Deeply understand your team

Having a deep understanding of your team is an absolute necessity if you want to have productive, insightful and positive one to one conversations with them. In the second instalment of our four-part series, we're looking at how you can start to truly understand people.

Part One of this series set you up for successful conversations with your team. You’ve learned about goal-setting, listening, choosing the right environment, asking questions, taking notes and staying vulnerable.

Welcome to Part Two. This one’s a daunting task, but it’s absolutely necessary for productive conversations.

You’ve got to understand your team members on a deep, personal level.

Here’s how you do it.

Know where someone is coming from

You can’t actively support and develop someone without understanding the journey they have been on. This context is vitally important: it will shape their thoughts, reactions and emotions.

Some things I try to understand:

  • What has their experience been like in previous jobs?
  • What was their relationship with their line manager then?
  • How did management behave in the business?
  • Why did they leave this job?
  • Who did they look up to? Why did they look up to them?
  • Have they always been in the same career?
  • What was their experience of education like?
  • Family & friends - what do they think about their chosen path? Are they supporters or are they detractors?

Two words of warning:

Understand that this stuff takes time. You obviously shouldn’t be immediately rattling these questions off to a new hire - it will come across as overly intrusive and creepy. Instead, put it together like a puzzle over the course of months - or even years.

Do this for the right reasons. If you ever feel like you’re trying to find out about someone’s background simply because you’re curious about their innermost thoughts and feelings, stop. You should be doing this to improve your ability to help someone, not to discover juicy tidbits of gossip.

Know where someone wants to go

When it gets down to it, the majority of people aren’t really passionate about their jobs. Startups love to wax lyrical about their “passionate, driven employees”, but being completely honest, I don’t think anyone works for CharlieHR because they’re fanatical about HR software.

Most people aren’t particularly passionate about their current job. People are passionate about their hopes and dreams. If you want to create true long-term motivation, you must build ways for your business to help your team members progress towards their aspirations.

The first step, of course, is understanding what someone’s hopes and dreams actually are. This means answering these questions:

  • Where do they see themselves in the future?
  • What are their immediate goals?
  • What type of remuneration are they targeting? What lifestyle do they want to lead?
  • Do they see themselves progressing on a skill based track or leadership track?
  • How ambitious are they?
  • How patient are they?
  • Have they found the thing they are best at?
  • Are they fascinated by another industry?

Unfortunately, if you directly ask anyone these questions, they’ll probably say “I don’t know”, or – even worse – will make up an inaccurate answer on the spot. Instead, give people space and allow them to rise to opportunities - and then ask them the question.

For example: someone in a junior role could be given a task outside their comfort zone – such as one with more responsibility, or one working in a different field. Then, after that task, you can ask them whether they would like to develop their skill in this area further. You’ll get a much more productive answer than just asking them out-of-the-blue.

Strength = Weakness

I’ve always believed that our strengths often manifest themselves as weaknesses.

Take me. I’m an empathetic individual.  This is fantastic when it comes to building great relationships with people on our team. It’s also a nightmare when I have to make hard decisions about the people I work with.

Another example: an old colleague of mine.

They were hell-bent on getting to an end result. They’d work with superhuman diligence and focus, and regularly completed seemingly insurmountable challenges. At the same time, this meant they had trouble with feedback, which they perceived as a barrier, disrupting their progress towards achieving a result.

When you’re having an in-depth conversation, understanding someone’s strengths, and how they can appear as weaknesses is a vital piece of information to hold in your mind. Knowing this will be able to provide criticism which feels positive, productive and informed.

It isn’t your job to fix the weakness. Most real weaknesses are deeply ingrained, and can’t actually be changed. Instead, focus on guiding both yourself and the team member towards an understanding of the weakness and its associated strength, and how it might impact their work and their team.


So now you know how to really understand your team. However, this information is useless unless you put it into practice - which is where we’re heading next. The next two articles will teach you how to develop your team through two key concepts: support and challenge.

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