The journey from colleague to boss

“What do you mean they’re testing me?” Alexandra was nearly shouting the question at me, the frustration and stress evident in her face.

She had inherited a team of former colleagues just two months ago and was finding her transition from peer to boss one of the most challenging of her career. After five years of success at a small cloud computing startup, Alex was chosen to lead the development team, succeeding her former boss, who advanced to the COO position. She had worked side-by-side with most of the team for the entirety of her tenure with the company, but they were now resisting her ideas about innovation. Alex had given several team members the task of investigating new technologies that could vastly improve the company’s flagship service. Instead of meeting the assignment with enthusiasm, her two former colleagues raised one excuse after another about how they didn’t have time for the project.

“Are they coming forward with solutions about how to free up time for such an important piece of work?” I asked.

“No,” Alex replied. “In fact, they don’t seem to care, nor do they want to let go of any other projects to make room for this one, which is critical to our long-term success. I never saw this side of them when we were peers. Now it seems they just want to work on their own pet projects rather than focus on what the company needs for success.”

“What consequences are in place if they don’t deliver on the project?” I asked.

“I guess I haven’t articulated any,” Alex said. “I see now they’ve been testing how far they can push me, and I’ve been enabling it because we used to be friends.”

Alex was experiencing what many people do when they lead former co-workers. Underlying her team’s resistance was jealousy mixed with a tinge of resentment and a lack of enterprise focus. Alex needed to address these issues promptly to get the team on track. She focused on six significant actions that made a difference:

1. Recraft their role point of view

The team behaved like a group of independent contributors with their own interests rather than as members of a larger whole. Alex held a team retreat to lay out the larger company strategy and explain the team’s vital role in achieving it. She described the importance of each person’s role, casting them as enterprise resources crucial to the company’s strategic success. She even changed their titles from manager to senior business partner to reinforce the importance of their positions.

2. Have the uncomfortable conversations

Alex had known many of her colleagues for years, and a few of them were also qualified to lead the team. She suspected there might be a bit of resentment on their part for not having been chosen for her position, especially because she was younger and had less tenure. It was time to talk about the elephant in the room. So, Alex spoke with each team member individually and affirmed her respect for their capabilities while acknowledging that she needed their expertise and support to make the department successful. She couldn’t accomplish it alone. Alex made her former peers feel seen and valued through this simple act.

3. Practice “Stop, Start, Continue”

To address the resistance to adding new projects, Alex and the team reviewed their current workload to determine where to focus their attention best. They evaluated their current projects and activities, identifying projects that should continue because they added value and those they could eliminate because they didn’t. That allowed the team to consider new projects they should start to drive innovation and deliver new services. The team discovered several activities that consumed time but produced little value, so these projects ended so resources could shift to revenue-generating activities.

4. Set expectations and timelines

In transitioning from peer to leader, Alex realized she needed to be clear about her expectations of the whole team and individually. She outlined an 18-month plan of key objectives the team needed to accomplish and established timelines, milestones and deliverables for each phase of work. Moreover, she reinforced the interrelatedness of their specific roles, encouraging better collaboration among team members and reducing the siloed behavior they had been demonstrating.

5. Hold them accountable

For the most part, team members responded to the new direction set by Alex, yet from time to time, she found it necessary to meet with specific direct reports to emphasize her expectations.

She made it clear that rewards would be tied to accomplishments and teamwork. Promotions and key assignments were reserved for team members demonstrating enterprise-focused behaviors. Alex gave herself a 6-month window to assess the talent on the team, after which she made changes where necessary, including the tough decision to let one person go.

6. Celebrate wins, even small ones

Alex knew the road ahead would be challenging for the team and wanted to keep them motivated. She made a point of celebrating their success at every milestone, establishing a practice of “weekly kudos,” where team members met for 10 minutes every Friday morning to acknowledge the contributions of their peers. Doing this weekly encouraged the team to look for good things to celebrate about one another, which engendered a culture of respect for each other’s capabilities and contributions.

This article was first published in SmartBriefs, February 2023.

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