We’re getting to the point of the year where the ‘newness’ has worn off and most people have forgotten what their New Years resolutions were. The excitement and vigor of your team around their personal and your organizational big picture goals has waned.

Maybe you already asked your team members what their ‘why’ was at the beginning of the year during your kick-off goal setting meeting. Maybe you had them put their ‘why’ on a postcard so they could look at it every day. Maybe you’re thinking you should ask them what their ‘why’ is so you can re-invigorate that rah rah feeling everyone had at the beginning of the year.

But consider this. Maybe the ‘why’ they gave you or will give you when you ask isn’t actually their ‘why.’ 😮 Maybe, just maybe, they gave your canned question a canned response. They said what they knew you wanted to hear or what they thought was professionally appropriate.

Think about it. When have you ever asked that question and had someone say, “My why is that I had passion once but my big dream didn’t work out so now I’m here because of the benefits and pay. But trust and believe if there’s EVER a chance my dream can come true, I’m out of here quicker than you can blink.”

No. Typically people say their ‘why’ is their family, or their desire to serve others, or some other reason that can easily tie to their job and satisfy their boss. And most managers and bosses are happy with that answer because it lets them think their employee will always be dedicated to their role. Until it’s the end of the year, and you missed your organizational goal even though everyone defined their ‘why’ and told you all the right things. Obviously there is a disconnect.

So what if you dig deeper. What if you have the guts to hear answers you may not like but will actually help you in the long run? What if asking just a few more questions lets you know how your employee views their role and whether they have actually bought in to your yearly goal or their own?

Here are five questions to ask your team members that will do just that.

  1. What about your role lights you up?

This question is going to reveal the guidepost you need to refer back to with your employee when their excitement, and maybe even results, begin to wane throughout the year. The answer might surprise you but knowing this will let you know how to better lead them.

2. What parts of your role feel the most draining or cause you the most frustration?

Yes. You need to go ‘there’. Often managers and leaders are afraid to ask this question because they don’t want to engage in a complaining session or encourage negativity. That’s why this question should be asked in a one on one setting. You’re far more likely to get responses that are thoughtful and heartfelt. You might find out there’s part of your process that your team member doesn’t understand but would never admit in a group setting. You also might find out your team member has a great idea that could help your process that you never considered and they never felt confident enough to share.

3. What trainings do you think we should provide more of or differently?

Spoiler alert: More often than not, their response to this is going to center on information or training THEY would like more of. So why not just ask them what training they feel they need more of? Because some of your team members may not trust you enough to be that vulnerable with you. Yet. The more conversations you have like this and the more open you are to feedback, positive AND negative, the more open and honest your team will be with you. But if you haven’t opened that door all the way yet, you need to ask this in a way that lets them off the hook of admitting they may not feel 100% confident in an aspect of their role.

4. When do you feel the most confident?

Resist the urge to tack on ‘in this job’ to the end of this question. If your team member responds they feel more confident doing something completely unrelated to their job, you now need to dig deeper. Asking the followup question of WHY will give you invaluable insight on how to help them translate that confidence into their role. And if your team member says they feel most confident in an aspect of their role, you may have found someone who can empower other members of your team to feel equally confident.

5. What is one of your proudest moments?

This may or may not give you any insight as to how your employee feels about their role or their goals. But it WILL give you insight as to what drives them in life and is a great opportunity to learn more about your team member. Again, lean into this question with a follow up question of ‘why’ if they don’t immediately offer up the reason. Approach this question with genuine curiosity and you are bound to connect with your team member. Also, the benefit of asking this question last is your team member will leave the conversation FEELING proud. It’s hard for people to reminisce about something they’re proud of without starting to feel that same pride creep in again. If they leave the conversation on that high, they’re much more likely to genuinely engage with you in the future because there will be a level of comfort and trust established with you.

Try these questions out and comment below which answers surprise you. And if you’d like more support and coaching on how to continue these conversations with your team, email me at hello@rosannagill.com.

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