New Favorite Leader Question_What is your greatest challenge right now_3x5 Leadership

My leadership by wandering around times, the time I dedicate to walking around my unit footprint talking to Soldiers, is not only a chance for me to take a break from the monotony of busy work but is in fact a very deliberate method to maintain my presence in the unit, which directly contributes to my team building efforts. Just as purposeful as the time I dedicate to my leadership presence and leadership by wandering around is the line of questions I leverage when talking to my Soldiers. The questions I ask when interacting with Soldiers are highly-focused and aim to gain new knowledge about something I want to learn about; this can include personal information about the Soldier, their feedback on our unit or recent training, or innovative ideas on how we can improve for the future.

My personal arsenal of questions can range from simple and vague (such as, “how is everything going?”) to organizationally specific (like, “what’s the thing we need to get better at now to become a better company?”) or even personal (“how was your and (spouse’s name)’s vacation to (location)?”). Each question serves a purpose, but are leveraged based on the Soldier, the current situation, and other contextual factors.

However, I recently found my new favorite question to ask subordinate leaders, such as platoon leaders or squad leaders, during these times: what is your biggest challenge right now?

This simple question can accomplish so many things for the leader you’re interacting with and your organization. Through it, you can solicit feedback while simultaneously help your people solve their current organizational issues. Below are a few of the greatest benefits that this question provides you and your organization:

  • You obtain bottom-up feedback. Answers help you identify friction points within your organization, whether they be at your or subordinate levels. With this new information, you can begin to target certain levels or areas in the organization with identified friction and challenges for improvement.
  • Get a pulse on your organization. By learning your peoples’ challenges, you find out what is important to them, what’s not necessarily going well, and can get a sense of the attitude that is permeating certain parts of the organization.
  • Initiate a coaching or mentorship relationship to tackle the challenge. Based on the context and scope of the challenge your people voice, you can immediately begin to coach or mentor that person through the problem. This does not mean that you take that problem to solve yourself; the responsibility is still theirs. However, you can offer support or guidance as needed, provide additional resources, or be the sounding board to create a possible solution.
  • Your people and organization get better. By voicing and identifying the issues in your organization, you get the ball rolling on solving them. After that initial question to identify the challenge, your follow-on interactions with that particular leader then become updates on the progress of resolving the challenge. This makes you and your people proactive in resolving challenges at your respective levels. After a few iterations of talking to one of your subordinate leaders about their current challenge, they will quickly learn to be proactive in resolving it rather than waiting for you to do it for them. Asking one of your people “what is your biggest challenge currently” for the third time will hopefully lead them to respond with not only identifying what the challenge is, but then offering what they have done about it already, what they are working to do next, and finally, what help or support they need from you if any.

I’d ask this question in a very non-threatening manner during low-threat times, such as to a platoon leader while in field as we wait for Soldiers to file through the dinner chow line, or to a squad leader if they stop by the headquarters area. You can also incorporate this question into your routine counseling and feedback sessions to add a bit more formality to it.

Moreover, this can be a question you ask yourself during your reflection or journaling time to have personal development impacts. This question can be a starter to get you to improve aspects of your own leadership.

So, I challenge you to consider how you can incorporate this question into your interactions with your people on a daily basis and make it a natural habit. You’ll be more informed of what’s going on in your organization and with your people, and you will collectively be more committed to resolving challenges at different levels to help your organization break the current limiting ceiling to get to the next level of performance and development.


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