
Are you undermining your team? You may think not – but they may answer differently.
I was once contacted by a frustrated leader. He had already lost one of his most valuable executives, and the rest of the team had fallen into an energy rut.
When he called me, Sam said, “I need to light a fire under these executives! They aren’t working to capacity. Can you come and do some team building with me to get this team back on track?”
But after a bit of investigation, I told Sam the pressing problem was not his team – it was him.
“Sam, I recommend that you and I work together to enhance your leadership,” I said. “Because, frankly, I believe that you are the problem.”
“What?” Sam sputtered. “What am I doing?”
“You are sabotaging your team with workarounds,” I replied. “You are undermining your executives’ authority,” I answered. “And it’s killing your team.”
“I don’t understand,” he responded. “I would never undermine anyone.”
“I know you don’t mean it,” I answered, “But it’s happening, and it’s serious. Let me give you just one example,” I said. “It’s always easiest when we take a real-time situation and dissect it so that you can see it.”
John, senior Vice President reporting to Sam, had shared the following with me:
Janet, manager of IT and one of John’s direct reports, was reticent to confront one of her employees on some poor behavior. As a consequence, things had reached a critical point. John urged Janet to step up and place her employee on a performance improvement plan – and Janet wasn’t happy.
In fact, Janet went to Sam, and she complained. Janet felt John’s edict was too harsh and Sam sympathized. Moreover, he overrode John’s directive and told Janet to forget writing up a performance improvement plan and just “work harder” with the employee.
When John found out, he was furious. Sam had disempowered John by getting in the middle.
“Well,” said Sam, “John was a bit harsh on Janet. I’ve known Janet a long time – and I think she just needs to work harder with the employee.”
“You aren’t hearing me, Sam,” I said. “You just disempowered John by doing this. Janet reports to John, right?”
“Well, yes, but…”
“Sam, when you allow people to work around their boss by coming directly to you, you are triangulating. You have created a conflict. Moreover, you have rendered their boss ineffective by showing others that they can just come to you when they don’t like a directive. And you have sent a clear message to their boss that you don’t trust them to handle things.”
Sam was silent.
“I have other examples, Sam,” I said. “You told me that Tim, your senior vice president of operations, has become disengaged. After a long conversation with him, he admits that you openly interfere with his decisions on even very small things, such as the color of paint in the bathrooms in the new offices. Evidently, you called the painters and had them change the color.”
“Well, yes, but…”
“Sam, if I came in and changed whatever directives you gave to your team, if I openly challenged your decisions on even the smallest things and went behind your back to alter things, how would you feel?”
“Oh.”
“Right,” I said. “The reason your team is disengaged is because you are actively disempowering them and they are simply giving up. One of your team members said, ‘Why should I put myself into this? Sam will just come along and change it and make me look inept.’”
Sam was, in fact, actively breeding mediocrity. No one wanted to fully engage anymore. They were loath to make decisions. One said, “I feel like a simple paper pusher. My people don’t respect me – they just run to Sam if they don’t like something I’ve decided.”
“Sam, moreover, you are thwarting your company’s succession plan – you are in the way of any true leadership development that can occur.”
Sam stared out the window. “But I’m not always in agreement with their decisions. Sometimes, I feel like they are going down the wrong track.”
“If you feel like that, Sam, this tells me that they haven’t received the expectations and mentoring from you that they need in order perform well – and this is where we need to work, now.”
Over the next few months, I worked with Sam and his team to set expectations around roles and responsibilities. We then worked on holding each other accountable in a way that mentored each to assume greater autonomy. As we used this framework, Sam became more comfortable with their decision-making. At the same time, I had to ask Sam to catch when he recognized employees were working around their bosses to come to him.
“Here’s what you do, Sam,” I said. “You redirect. You ask them to go back to their boss to solve the problem Whatever you do, you mustn’t give them the impression that you will step in the middle. Support your people.”
This was hardest for Sam to do – he had received great affirmation by having people come to him with problems. But he had to let go and take on a new approach with his leadership to empower and support his team so that they learned how to do the same for their own teams.
If you are a workaround artist, stop it. You are eroding your team’s credibility and engagement, and long-term, driving mediocrity as leadership culture.
And if you have a boss that is a workaround artist, you need to have a talk. Tell him or her that you are working on your own team-building, and that you recognize they need to respect your authority. Say that in order to do this, to please redirect your team member back to you, and to give support to your leadership so that you can be effective.
This is a tough conversation to have – but unless you do it, you will continue to disengage and feel helpless in the face of big decisions.
What has your experience been with workarounds? Let’s keep the conversation going.

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