In the first three articles in this series, I wrote about the classes I will teach in 2027 at the Securities Industry Institute at Wharton on life, career, and leadership. The final class focuses on having difficult conversations and influencing people they cannot direct.
We will begin with psychological safety.
People need to feel comfortable raising concerns, disagreeing, and giving honest feedback without fear of embarrassment or retribution. When people are afraid to speak candidly, important information gets withheld and problems can go unaddressed.
Leaders have a significant influence on whether people feel safe speaking up. Employees watch what happens when someone challenges an idea or brings forward bad news. A defensive or dismissive response teaches people to remain quiet. Listening carefully and treating the person with respect sends a very different message.
Even in an environment with a high level of psychological safety, some discussions will be uncomfortable. People sometimes need to raise an issue that would be easier to avoid or give someone feedback that may be difficult to hear. Having those conversations early is important. An issue that could have been addressed relatively easily can become a serious and expensive problem when people avoid talking about it. Think about a conversation you know you need to have but have been putting off. What is keeping you from having it? And what is likely to happen if you continue to avoid it?
Preparation is also important. I use an idea I call Humble Confidence.
Before having a difficult conversation, separate what you know from what you are assuming. Be especially careful about assigning motives to the other person without knowing whether your assumptions are correct. Go into the discussion prepared to make a strong case while remaining genuinely curious about what you may not understand.
We will then focus on how to have the conversation directly and respectfully.
When giving someone difficult feedback, the goal should be to help them grow and improve. Explain the issue clearly and listen carefully to the response. What you hear may change your understanding of the situation.
Many of the same skills become essential when someone needs to influence a person they cannot direct. People at every level depend on peers, senior leaders, vendors, and others over whom they have little or no formal authority.
Influence begins with getting clear about the result you are trying to achieve.
From there, the focus shifts to the person whose support you need. Understanding what is important to them and how they are likely to view the request can help determine how to approach the discussion and make a stronger case.
Credibility also plays an important role. People are more likely to listen when they trust someone’s judgment and believe that person understands the issue. Credibility is built over time through the quality of someone’s work and the way they interact with others. When their support is needed, the reputation they have already established comes into the room with them.
In the class, participants will apply these ideas to a real influence challenge.
Readers can try a version of the exercise as well. Think about someone whose support you need but who you cannot direct. Before deciding how to persuade them, look at the situation from their perspective. Consider what is important to them and how they are likely to see your request. The better you understand their position, the better prepared you will be to make your case.
My goal is for participants to leave the class better prepared to handle conversations they might otherwise avoid and more effective at influencing people they cannot direct. Both skills take practice, but there are probably opportunities to practice them in your organization right now.
As you prepare for next year’s strategic planning, you’ll have important choices to make about where to invest your organization’s limited resources.
Understanding where your competitive advantage comes from can help you evaluate those choices and determine which opportunities deserve your attention.
On October 22, I’m hosting a free 45-minute webinar where I’ll share the approach I use with leadership teams to think more strategically and prepare for a productive strategy session.
