10 Questions to Prompt Your Team Leader for Career Insights

10 Questions to Prompt Your Team Leader for Career Insights

Regardless of our career ambitions, we all have goals. We need to know how to leverage our unique talents and harness our weaknesses to achieve these goals. The most likely source of insight and guidance, particularly in the shorter-term, is our team leader. Not all leaders are attuned to the individual development of their team, so it can fall on you to help your leader to help you. Here are 10 questions you can use to start a conversation with your leader, one that will provide career insights for personal branding

  1. How can I help the team be more successful?

Start with an easy question that engages the leader in their own priority – the team.

  1. How would you describe my personal brand?

Personal or self-branding is a watch phrase right now, and you need to know if you are successfully developing a signature and reputation that will work for you and your long-term goals.

  1. If I double down on a strength, which should it be?

This question solicits information about your abilities that can lead to insights about your role in the team as well as how you are appearing in the group. You might even ask your leader about particular strengths for closer insights. 

  1. If you were in my shoes, how would you leverage my strengths?

A similar question, asked in a different way, can often get a fresh answer. Engaging your leader about their own skills will help them to relate to yours and provide useful guidance.

  1. Do I need to change anything?

This is a difficult conversation for leaders to have with team members because it’s not always easy to hear the answers. It is critical to gather information about your (actual or perceived) weaknesses that may be having a negative impact on your brand or be a missed opportunity. 

  1. Where should I be visible to help the team?

You need to know what opportunities are available and useful both in and out of the organization so that you can apply yourself to taking advantage of them.

  1. Who should I be talking to inside or outside of the company?

For your own development and the development of the team, you want your leader to name names. Be specific about your motivation – there is only partial overlap between a resource for the team and one for your own growth.

  1. What meetings should I attend?

Your leader is well-positioned to know more about your industry, and may also know about your other interests. Their thought leadership can benefit you through career development and networking opportunities.

  1. What relationships should I be building?

From a mentor to a champion or simply a good career resource, there are people your leader may know who can help your business development. Be specific about the various roles you are looking to fill in your career so your leader knows what types of suggestions to make.

  1. Can you recommend what you think I should work on specifically for the next 90 days?

You need to give your leader a chance to offer you actionable guidance instead of an opinion. Finishing out any conversation with this question will set you on a measurable path that you can revisit with them after the time has passed. It is an effective way to be an intentional entrepreneur.

When approaching your leader for help in your professional growth, be mindful of timing and phrasing. While a periodic review is a good opportunity for these conversations, consider a less formal meeting to engage in a dialogue. Your leader has every motivation to help you to succeed; you simply need to give them the opportunity and the prompts to act on it. 

Are there challenging conversations that you need to have in your life? My new book Listen: How to Embrace the Difficult Conversations Life Throws at You dives into tough conversations and how to have them. Join the waiting list for your copy.

© 2020 Jennifer Dalton

Jen Dalton is a personal brand specialist with entrepreneurship in her DNA. She helps business owners and executives define how they show up as leaders, make the most of their strengths, and tend to their legacy, growth, and visibility. The author of two books, frequent speaker, podcaster and “Purpose Sherpa,” Jen is a critical resource for any person or company that wants to define their brand and differentiate themselves in authentic,  credible, and relevant ways to the market.