Want to Win Respect and Help Coworkers? Try Challenging Them.

If only I had a dollar for every time I heard leaders say they want the people in their organizations to “tell me what I need to know, not what I want to hear.” The ability to speak truth to power is easier said than done, but people who can do it well earn respect from their managers and help their own careers in the process.

The same principle applies when leaders want to develop professionally. Sure, many leaders I work with appreciate having a safe, supportive and non-judgmental environment to experiment with new ideas and explore aspects of their own leadership styles. But the same leaders tell me that what they want most from others is constructive challenge from the people around them, whether it’s on the job or in a formal learning setting. The reason, they tell me, is that constructive challenge pushes their thinking and their emotions in a way that drives positive action and growth.

And the more senior the leader, the more this seems to be the case. I see this often here in Asia, where cultures can be more hierarchical and relationship-focused than in the relatively egalitarian and task-focused cultures of many Western countries (leaders tend to receive less upward feedback in hierarchical cultures).

 So, what does it mean to give someone constructive challenge? I ask this question regularly in conversations and leadership workshops I facilitate. And over time I have compiled a list of common requests I hear leaders make. Here are a few of them:

• Ask pinpoint questions
• Prompt me to consider new options
• Ask for the facts behind my statements (don’t take my word for everything)
• Give me a point of view different than my own
• Ask me to consider others’ points of view
• Give me “quick responses” to keep me alert
• Help me visualize and consider the future
• Tell me if I am speaking too much
• Point out possible assumptions and biases
• Give me candid feedback about how I am coming across to you

 Similar to the advice given in the HBR article “Connect, Then Lead,” my experience is that first offering warm support and then showing strength through constructive challenge works best. I’ve seen firsthand how doing this earns respect, strengthens relationships and propels people to take action to develop themselves.

 Now I'll ask you. What have others done to constructively challenge you? And how did the experience impact your or your relationship with the person who gave it? I look forward to hearing your stories and experiences.