I was so angry I was afraid the client I was on a call with would see the steam pouring off of me. A new team member and I were pitching for a contract and said team member was nowhere to be found. Nada. Nowhere. No word. Not on the call.
I gamely carried on with our meeting wondering when he would show up.
Which is when he did, messaging me he didn’t have the call information and could I share it with him. All this while I was pitching to the client.
Eventually, he joined the call and the pitch went pretty well, all things considered. But it left me scratching my head. Especially when in a debrief call, my team member said he’d ‘try’ to be on time from now on. His apparent lack of concern for being late to a client call definitely did not match mine.
Try?! Being on time for clients is a non-negotiable for me.
Which got me thinking and which ended up being the genesis of this post.
It’s why I’ve come to strongly believe that you should always date your co-workers.
And by dating I mean test the waters with them before jumping into high stakes situations.
You wouldn’t commit to spending your life with someone without dating them first. And yet, in the workplace, we often jump into high pressure situations with colleagues we don’t know well.
That’s why I combined the “21 questions to ask when dating someone” with my experience working with teams, to design a new list of go-to questions.
We could all do with some fresh perspective when it comes to ourselves and our team members. Use the questions to ‘date’ your team members – get to know them in the process so when the stakes are high, you’ll have a firmer foundation to work from.
Here is a list of 25 questions I’ve designed for you to ask new team members when you’re ‘dating.’
If you are working with a new team member, a new team, here are questions to ask each other to help prevent the situation I found myself in above.
Because great teams tend to know each other well and because we’re about more than just our work, I’ve divided the questions into two parts, those that are a bit more personal (don’t worry, nothing too HDR [heavy, deep and real]) and those that are directly work related.
Let’s dive in with the personal questions first
- What’s the latest movie or book you read?
Let’s ease in gently. This is an easy question that will give you insight into their tastes.
2. Who would you most like to sit next to on a 10 hour flight and why?
This one’s straight from the dating questions and is a fun one because it’s broad enough for them to answer as they wish (super specific, in general, etc).
3. What is the non-TLDR (too long didn’t read) version of your life? In other words what’s the shortest possible version of your life story?
This one is aimed at uncovering how they summarize their life so far and what they choose to highlight. Is the version funny, sad, full of struggle, triumphs, achievements etc?
4. What is a cause you believe in?
Be prepared for wildly differing answers with this one. It will help you understand what’s important to your team members.
5. How useful would you be in a zombie apocalypse?
I borrowed this one straight from the dating questions, ‘cause why not. It’s fun and enlightening.
6. How much do you know about the world outside your country?
Again, this one is straight up from the dating questions. It will give you great insight into what they do or don’t pay attention to in the ‘broader world.’ Their answer can help you understand their focus – whether it be family, community, country or global.
7. If you could live your life again knowing what you do now, what would you change?
Direct from the dating questions again, this one is epic as it will show you what they’ve learned, what they’d like to change and more. It’s also broad enough that they can answer as lightly or personally as they wish.
8. If you could be born again and choose what nationality, gender, and race to be, what would you choose?
Another direct from the dating questions, this one packs a punch and will give you some insight into their awareness of power and privilege issues.
9. What’s one of your best and one of your not so great habits?
This question will quickly demonstrate both their level of self-awareness as well as what they consider to be a good and bad habit.
10. What motivates you? What tends to demotivate you?
You’ll uncover gold here. Make sure to put their answer in your pocket for later on when a team member may be stressed, lagging or overwhelmed. You’ll have a custom-made solution for how and how not to motivate them.
11. Do you tend to be introverted (you refuel by being alone or in a small group with people you know well) or extroverted (you refuel by being in a group)?
This one is great again for sussing out their self-awareness and for knowing how best to approach them in the future when they’re tired and in need of rejuvenation.
12. What are two things you know how to do that would likely surprise people?
This is a good transition to our next batch of questions, which focus on the world of work. It’s also interesting to see how they answer you – do they describe hobbies, work related things etc?
I’ll share those questions in the next blog post
There you have it for now. May this part one of a two part list of questions designed to help you ‘date’ your team members, help prevent you finding yourself on a call with an important client with your team member nowhere to be found. Have fun asking and answering the questions and file all your new gems of information away to help improve communication, collaboration, teamwork and ultimately help you work better together. High five to that!
And be sure to check out part two which dives into specifically work related questions.
Now go on and learn, laugh and lead
Learn
- Check out the resources I used in writing this post: Quartz article Abby Falik, founder and CEO of Global Citizen Year, via Alexandra Samuel
Laugh
- Chuckle as you watch Wellington the penguin explore the zoo, from outside his enclosure. North meets south when he (from the south) and beluga whales (from the north) see each other for the first time. There’s always room for a fresh perspective.
Lead
- Use the list to ask questions of your new team members or even your old members, as there’s always some fresh perspective to be had.
P.S. Curious to know more about your worldview and perspective? Check out my Life Lense® online assessment.
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