"Tell Me Why My Plan Won't Work."

By Tom Tischhauser

February 14, 2023

Estimated Reading Time: 4 minutes

"Tell Me Why My Plan Won't Work."

It was our January kickoff meeting. 147 officers of the company were gathered to review the previous year's results and the vision for the year in front of us. As always, in addition to business unit presentations, there would be guest speakers to talk about current trends, new technologies, and give motivational messages.

To start the meeting, our CEO walked out to the center of the stage, accepted well-deserved thunderous applause, then stopped at the podium. He let the silence settle in, looked over the audience of leaders, and opened with something like this: "I was under the impression that we had smart leaders in our company. Apparently, we do not."

He put up a slide with the prior year spend on consulting companies that included McKinsey, The Boston Consulting Group, and Booz Allen. He continued, "It appears to me that our leadership group has lost their confidence and cannot make a decision without validation from outsiders. Further, I find it a waste of my time, and yours, to be interviewed by these consulting firms only to have our positions used in the final report to justify their concurrence with our directions."

He let his comments sit for what felt like an eternity. He finally broke the silence with the new policy. "Effective immediately, all strategy consulting agreements must be approved by me. And, they will only be approved if the statement of work is to highlight all the reasons that our strategy will not work. The work product from these engagements will tell us why our plan of record, or proposed directions, are incorrect or vulnerable." We were in the presence of wisdom and humility. He challenged us to dare others to find the weaknesses in our plans and assumptions. He challenged us to make our plans better and bulletproof. He valued diverse points of view to find vulnerabilities and opportunities for improvement that we had missed.

To create a culture of productive criticism in your organization, have your leaders challenge their teams to focus on all the reasons the plan could fail versus looking for accolades from "yes men" or groupthink. Imagine the organization that embeds this culture of find, fix, and improve. How productive would it be for teams to crave feedback from diverse points of view and experience with industries, technologies, and trends?

Encourage your staff to embrace the same culture for their leadership style. Coach them to seek feedback and insight on how to be more effective. What I have found over the years of leadership and executive coaching, is that everyone says they want feedback...until they get it. In all cases they feel stung, defensive, and blindsided. The reality was that they were challenging and daring their colleagues to find gaps in how they lead, assuming that nothing could possibly be identified.

Here are 3 steps to incent your people to seek input for their plans and leadership styles:

  1. Make the challenge clear. Create a session to specifically identify vulnerabilities in the plan that could impede success. Being specific about the objective of the session creates a safe environment for productive criticism. In general, people are polite by default. This atmosphere requires honest, candid feedback and minimizes any perception of profession or personal attack.
  2. Once the areas of concerns have been addressed, the next phase is improvement. How can the plan be improved? Build on the solid base created in Step 1.
  3. When the team members see the benefit of critique and improvement on the work plans, encourage them to treat their leadership style in the same way. Start this process by asking for feedback on your leadership style. Specifically ask your team for 2 or 3 things that you can do to improve.

Our CEO saw that winning made us vulnerable. We were afraid to fail once we were at the top. Seeking outside feedback was the right step. The statement of work was wrong. We were seeking validation, not critique. Use the same process for your performance talent-development plan. Be specific:

  • How is my style impeding you?
  • How can I change to enable you to contribute more?
  • What areas of development would I benefit from?

Asking for general critique and feedback will typically yield a polite and reinforcing response. Be specific and challenge your teams to find the weaknesses in your plans and leadership style. In time, this process of continuous improvement through candid feedback will become the winning culture.

Tom Tischhauser is an Executive Coach at Wynstone Partners. Tom specializes in 1-on-1 executive coaching, public board reviews, and creating custom speeches for organizations. Tom believes in coaching successful business leaders towards success, because successful leaders breed successful business.