How to Lead Teams When You’re Hard to Please

Photo by Syed Ahmad on Unsplash

Do you identify as an intense, passionate leader with sky-high expectations? Are you afraid that being “too compassionate” or “too empathetic” will mean that your teams won’t hit their deadlines and milestones? On the other hand, are you worried that you might come across as a dictator and inadvertently be shutting down creative ideas and innovation?

Many of us struggle to find the right balance for a leadership style that is both supportive AND pushes for the highest quality standards. Try these three strategies for a different approach that inspires your team to get results.

1. Slow down to build trust one person at a time

Yes, you might be an intense, passionate, and emotional person. It’s hard to turn that intensity down when you’re excited about an idea and want to push forward to define what’s next. However, your ideas and expectations will be more widely accepted if there is high trust between you and your teams.

In addition to the presentations, meetings, and high stakes conversations, also slow down and spend the time to build trust. The easiest way to connect during 1–1 conversations with your people. One handy rule of thumb is to open the conversation with topics that are outside of work. Spend the first five or ten minutes of the meeting build trust before diving into the to-do list of problems or deliverables to be discussed.

One of my clients, let’s call her Jingyi, is a first generation immigrant and new to American culture. She often bemoaned: “I’m terrible at small talk,” yet know that as a vice president at her enterprise software company it was crucial that she build relationships with her peers and the executive team. We developed a system to talk about non-work projects across the following themes, with some example questions:

Social & Cultural Events

  • How did you spend your time this past weekend?

  • What do you do for fun?

  • Did you watch the Superbowl / Oscars / news about the Elizabeth Holmes trial?

  • What stood out for you from our last offsite / dinner / lunch & learn?

Family & Pets
Pick up on cues from peeks into their personal life during these zoom times. Are there photos or indications of who they live with? You can ask how their kids are doing in school or how puppy training is going. Or, if they are typically off-video or with a blurred background, know that they may be less comfortable talking about these personal topics.

Mutual Passions
Figure out what you might share as a mutual passion. Perhaps you’re both foodies or love to travel. Perhaps there’s a shared love of music, shows, or artists.

Work Related Opinions
These aren’t directly about the work, but more to get a sense of shared common ground and to better understand the other person’s perspective of the world.

  • How do you feel about our new CEO?

  • What did you think of that last presentation?

  • Did you see that the company is offering a new health benefit?

Personal / Vulnerable Check-Ins
This category can feel a bit more intrusive but is helpful when you already have built up some trust. These topics are better for ongoing 1–1s especially when the person has indicated that they are more open to discussing these topics.

  • How are you coping with the rapid pace of this project / new COVID restrictions / the new in-person schedule?

  • Is there anything I can do to support you?

Finally, when building trust, the #1 way to get someone to open up is to first share something personal and specific. You can set the tone for the conversation by going first and sharing how you feel about any of the above topics. The other person’s response will give you a hint of whether they’re also eager to share and connect or if they’d prefer to move on to the next agenda item in your 1–1.

2. Listen first in team meetings

Many leaders who have sky-high expectations can tend to command and take control of a team meeting. We assume that setting the agenda and clearly laying out the expectations will make it easier for others to follow our lead.

If you’re hard to please, it can be difficult for others to continually listen to what they perceive are unrealistic expectations or a leadership style that doesn’t leave room for other opinions.

Instead, try a different tactic and take a back seat in the team meetings. You could try:

  • Asking open-ended questions and truly listening to what others have to say. If this is a new communication style for you, you might have to pick a trusted team member and ask them to go first in answering the question. Alternately, call upon someone who is comfortable giving an answer on-the-spot.

  • Have someone else run the team meeting and set the agenda. Consider rotating this role between team members.

You can always summarize the meeting and clearly set out next steps and expectations moving forward.

3. Match your people’s communication and emotional style

You work with a number of different team members. Think about the people who you have instant chemistry with. These people are likely to have similar communication and emotional styles to yours. For example, f you are a person who is direct, pragmatic and caring, you likely have an affinity for others who share those values.

To be an effective leader, focus on building range. You can be more intense and direct with people who are like you. For other quieter team members, this intensity will shut them down. Try to match the other person’s communication and emotional style and act in a way that gives them space to process information in a way that’s comfortable for them. For example, a quieter leader may feel the pressure of having to come up with a brilliant answer on the spot. Instead, give them the space to consider the question and share their thoughts with you later on.

Bottom-Line

As an intense, passionate leader you can both have high expectations AND practice the servant-leader mindset of being compassionate and empathetic. Experiment with showing up differently as a leader by 1. Slowing down to build trust one person at a time, 2. Listening first in team meetings, and 3. Matching your people’s communication and emotional style.

Tutti Taygerly