Managing challenging people

Challenging team members are common, but managing them is anything but straightforward.

Leading and managing people can be tough because each person is unique, coming to work with their own individual preferences, personalities, and history. Leading and managing a software team is even harder because the work requires individual team members to work together on the same system and you can’t predict how those people will interact.

Software engineering leaders often ask me how to deal with especially “challenging” people. Here are some tips on how to manage this well.

Diagnose what you mean by challenging

Before you can find an appropriate management approach, it’s important to dive a little bit deeper. A “challenging” team member may require more work from you, but it’s first important to understand why. 

Here are some areas to explore:

• Contrasting preferences – When people approach situations differently, especially to you, you might feel like you have more work. I remember working in one team and despite the number of emails I sent about a specific topic, I still needed to talk to a team member through that topic in person – they just weren’t very good with keeping on top of their inbox.
• Contrasting cultures – Team members with a different culture will often approach situations differently. Many years ago, I worked on a team in Denmark and was initially stunned by team members being extremely vocal and direct about their disagreement with a solution. As an Australian living in Britain, that directness felt jarring to me.  
• Ineffective communication – I’ve seen firsthand when a team member talks over other people in the team, or when another team member seems to take over the team meeting as they air an internal monologue to think. Underdeveloped communication skills can make a team member more challenging to work with and lead.
• Trust issues – When someone lacks confidence or is unsure of themselves, this affects how they interact with the team. Sometimes this means they work as much as they can in isolation, share minimal information about work, and are reluctant to ask for help.

Although the example areas listed above are representative of challenging people, it’s also not meant to be exhaustive. Before you act, first think through some of the possible causes for viewing them as challenging.

Focus on the behavior, not on the person

It’s very human to quickly label what someone does and to confuse it with the person. Just like effective feedback, focus on what someone is saying or doing to understand how you might start a conversation about this. Most people are unaware of their actions. Be careful not to generalize or stereotype them based on a few of those actions. When you label someone as rude, inconsiderate, or aggressive, confirmation bias can kick in and you’ll notice behaviors that reinforce your conclusion.

Here are a few examples of how you might reframe labels to focus on behavior:

• A “rude” person – A person who interrupted three team members in the last retrospective.
• An “inconsiderate” person – A person who started three work items in the last week, leaving a junior person to finish work that appeared boring and repetitive.
• An “aggressive” person – A person who gave a very detailed 15-minute critique in the last team meeting when someone proposed a design alternative.

Once you’ve identified the behavior, your first step is to practice radical candor, bringing their actions to their attention and detailing the impact it is having on others. Most team members are trying to do their best, but often are not thinking specifically about what they do, the appropriateness of their actions, and potential consequences. 

Explore how you can support them

Although offering direct feedback early and often can remedy a lot of challenging behavior, it’s not your only tool. To help someone improve their effectiveness, sometimes the most appropriate thing is to change the way that your team works. 

On one team in the past, I was working with a person who tended to think by talking. This manifested a lot in team meetings, where they would typically talk the most in team meetings, particularly in system design discussions where they had strong opinions. We discussed their needs and experimented with splitting design meetings into two parts. In the first part, we would meet to outline the situation, and brainstorm possible approaches. During brainstorming, we asked people to pause any criticisms and only asked for new ideas or possible alternatives. We then paused the discussion so that team members could reflect on all options. This pause also gave this person a chance to talk with another team member (but not take over the team meeting) to think. This allowed them to better summarize their thoughts in the second part. The second part gave everyone an equal chance to share their opinions, concerns and to try to reach an approach everyone was comfortable with. 

Remember that your team environment is likely shaped by your background and your preferences. Given that each person is very different, with different preferences, backgrounds, and experiences, some team practices and processes may simply be more difficult for someone to adapt to, so consider how these can be as inclusive to all preferences where possible.

Consider a time budget

One trap many early leaders fall into is spending too much time focused on the challenging person. As a leader or manager, you are responsible for the entire team and if you find yourself spending significant time investing in only one of your team members, it’s likely you’re neglecting support for others and other things that need your attention. 

To remedy this, remind yourself that you are working with adults in a professional work environment. Your role is to support them so they are successful, but consider the fine line between supporting someone and coddling them. 

If someone appears to be challenging, your role is to discuss this in a radically candid way (be empathic and direct) but to make sure they take ownership of their own success as well. Consider being clear about the time investment you can offer them to help them be successful.

Challenging people don’t have to have to be a challenge

Although managing challenging people might seem like a challenge, it doesn’t need to be. Remember that your role is to help them be successful, and to do that, you need to prepare to discuss how they come across as challenging to you or other team members. 

First, think about the contributing factors to why they appear challenging. Be radically candid in the feedback to them and explore how you can best support them. Finally, consider a time budget and be clear with them about how much you can help them smooth out some of these rough edges.