Work conversations are often “shallow”: sterile, devoid of meaning or feelings, scripts that everyone knows. It doesn’t have to be this way, so let’s shift the conversation and go deeper.
Here are five simple, ready-to-use ways to make every conversation deeper at work and make more authentic connections with others.
1. Stepping beyond “How are you?”
Most conversations between two people include the oft-heard, “How are you?” When you ask, you’ll likely get a short answer (e.g., “Fine”, “Good”, “Meh”) that appears to end the line of discussion.
So, let’s change that.
Take the next step
Instead of accepting what you hear as the end, use it as the beginning. I often ask, “What makes you $THEIR_REPLY today?” For example…
- I’m curious, what makes you “fine” today?
- Would you be comfortable sharing what’s helping you feel good today?
- I’d love to hear more about the “meh”.
After all, you asked how THEY were, and they told you. Honor that response, don’t ignore it, and take the next step to understand why they are that way.
Then shut up, and listen. Don’t interrupt.
And listen closely for an opportunity to ask a follow-up question about something that intrigued you.
“Thank you.”
However you decide to end that line of conversation, thank them for sharing with you. They took a chance to deviate from the script, to reveal more about themselves to you. That’s a risk worth appreciating.
2. Spotting Strengths
Next, I’ll show you how to get someone talking about their strengths. Let me set the scene:
Sue is having a weekly 1:1 with Mike, the Lead Programmer on the team. Mike reports that he finished three complicated PR reviews last week and is looking forward to more coding this week. There are seven programmers on the team, and teammates often ask Mike to review the “tricky” PR’s, or those that impact core areas of the product. Though Mike sees this as part of his job and doesn’t mind doing it, it’s both tiring and derails Mike’s own coding work.
There are many ways to respond, but only one goes deeper:
- Boredom: “Ah, glad they are behind us. Where are you with finishing FOO?”
- Frustration: “Dang it, I told folks to review each other’s PRs so you can focus on finishing FOO.”
- Gratitude: “Thanks, Mike, I appreciate you keeping an eye on things.”
- Amazement: “Three! Wow, that’s a lot more than usual.”
- Spotting strengths: “Really… how did you do three in one week?”
Although you may use all these at times, depending on the three factors of congruence (you, them, context), I think a “spotting strengths” stance is often overlooked. When you ask “how” someone did something, and remain curious, both you and the other person may learn something. Let’s see how Sue does this…
Sue: “Really, how did you do that many in one week, Mike?”
Mike: “Well, I just sat down and did them, I guess. I knew they had to be done.”
Sue: “I rarely see someone doing ‘grunt’ work with such a good attitude. I really appreciate that.”
Mike: “It’s no big deal, my father always told me ‘being the boss sometimes means cleaning the toilets.’ So, though it’s not fun, I’m not above doing it. It’s necessary to support the team.”
Do you see the formula?
Sue’s responses capture the formula for spotting strengths. There are five steps:
- Listen carefully to what the other person is saying, how they are saying, and what they are really communicating.
- Commit to curiosity about “how” something was done.
- Listen for some strength the person exhibited.
- Point out the strength as though it were extraordinary – because it is! (All strengths are!)
- Listen more… return to step 1
Sue chose to comment on one of the strengths she noticed (“willing to do grunt work with a good attitude.”) She’s right – it is rare, and worth noticing.
Sue could have also commented on…
- Mike’s leadership in keeping the codebase clean, rather than insisting on only adding new features.
- How PR review supports the team’s growth is by providing feedback to other engineers.
- Mike’s professionalism and drive, which relieves Sue from having to nag him about PR reviews.
- A multitude of other strengths Sue can identify and appreciate
Why this matters
Did you notice how much Mike revealed when Sue showed just a bit of care and curiosity about him? He discussed his Father, from whom he learned to be a leader, his own leadership philosophy, and the early life lessons he had learned. That is a rich vein to mine that will lead to knowing Mike better!
Also, imagine how Mike feels about Sue after this exchange? I’m guessing “seen, heard, valued, appreciated, open, warm, and trusted.” Mike’s relationship with Sue has improved, and has new depth to continue going deeper. And, Mike
And what about how Mike feels about himself? Words like “proud, confident, competent, influential, trustworthy, excellent, and positive” come to mind. Mike’s self-esteem is be a bit higher, putting him in a better position to navigate the challenges of work and life.
Evoking strengths, so you and the other person recognize them, builds positive self-esteem and system-esteem, improving the functioning of the whole system.
3. Build resilience and capacity
Let’s talk about the follow-up question that builds both resiliency and capacity.
Let’s set the stage again:
During Sue’s 1:1 with Ana, a Senior Programmer on her team, Sue asked Ana how she helped the team navigate a conflict about upgrading Go libraries. After highlighting the strengths Sue spotted and appreciating them, Sue asked another magical question: Where did you learn that?
Ana recounts that she took a conflict resolution course a few years ago and remains interested in the topic. She used to be afraid of conflict, but now sees it as “energy for change”, and was excited to help the team navigate this situation.
Sue was surprised and pleased, and told Ana how much she appreciated it. In fact, she asked Ana to teach her the basics, as she also didn’t like conflict. Ana felt honored and enthusiastically agreed!
You probably get the point: when you catch someone doing well, ask where they learned it. It’s just that simple.
But also… It’s profound. Why?
Because the question unlocks some profound conversations…
- Because we categorize people so often in our society (and at work), it emphasizes the role of learning over “being” a particular kind of person. Emphasizing that a skill or mindset can be learned reminds both Sue and Ana that people can change.
- It flies in the face of traditional corporate “wisdom” that says “people are nothing more than their role and level.” Resolving team conflicts might be considered “manager work”, but Sue sees beyond Ana’s categories and instead sees Ana as a whole person.
- It empowers people to bring their whole selves to work, rather than just their “hands.” Instead of Sue saying, “Oh, that’s my job” or “I’m sorry, I should have done that”, Sue normalized that team members are capable of helping themselves and others.
- It reduces the team’s dependence on the manager and emphasizes that everyone got to where they are through learning, rather than being born a certain way. After all, no one comes into the world knowing Python. 🙂
- It normalizes learning, which is vital to team growth.
- It flips the power hierarchy between the manager and employee. By asking “Where did you learn that?” the manager is admitting they don’t know something, and only the other person can help them.
Oh, and how do you think Ana felt during this conversation? Words that come to my mind are “honored, seen, appreciated, useful, valued, unique, whole, and connected.” I suspect Sue felt the same.
These “deeper conversations” aren’t tricks, but they are simple ways to move off script and make meaningful connections with others. If you haven’t noticed, you can use these with your partner, kids, parents – or even your barista!
4. Invitation and Promise
Now let’s deconstruct a conversation I recently had to illustrate another way to go deeper in your conversations – and create a learning environment.
Patty: “Marcus, what I want is for you to be more direct, more yourself. I need your strength, boldness, power, focus, and opinions that you seem to hold back. Too often, I get a sense you’re making yourself small, trying not to take up space. But, it will work better for me if you bring your masculine energy, instead of being tentative and insecure.”
Marcus: “But… what if I don’t… or… can’t… do that?”
Patty: “That’s fine too, and I’ll still like ya. I’ve said what I hoped for, even though I know I might not get it.”
This conversation (based on real life) is an example of two ingredients that create an environment for growth: an invitation and a promise.
As leaders/managers/bosses/consultants, people often expect us to tell them what we want and need from them. And, we might get the impression that’s our job – to tell others what WE want and need. So, we might fall into the habit of telling (also referred to as announcing, proclaiming, dictating, directing, “passing down”, etc.)
And, taken alone, the first part of the conversation could be seen that way…
The promise that changes everything
When Patty told me what she wanted from me, a knot formed in my stomach. I pasted on a smile and braced myself, unsure what was coming.
Hearing it, I could have responded in many ways. All four incongruent coping responses (blaming, placating, super-reasonable, and irrelevant) were all options I know how to use. I could have said…
- “Patty, if you weren’t so pushy, I’d have a chance to think.” (Blaming)
- “Patty, you’re right, I’m so sorry. I’ll do better at that.” (Placating)
- “Patty, I can think of three times I was strong, two times I was bold, and once when I was focused.“ (Super-reasonable.)
- “Patty, the fact is that ‘masculine’ and ‘feminine’ are societally constructed concepts which may not have a place in post-modern life. Let’s dig into why…” (Irrelevant)
But in that moment, I felt only one concern, deep in my gut: How safe was I? What would happen if I couldn’t give Patty what she asked for?
So, I had to ask her… what if I didn’t give her what she wanted?
Patty’s reply was the promise that changed her words from “telling” to “inviting.” It shifted her request from feeling like a “mandate” to an “invitation.
She said, “That’s fine too, and I’ll still like ya. I’ve said what I hoped for, even though I know I might not get it.”
Wow. Take a minute and process that. How often does someone tell you they wish you had acted differently… but they will still like you if you don’t?
That’s powerful acceptance, devoid of judgment.
Simply by accepting me the way I am, Patty let me know…
- She was okay with not getting what she asked for.
- This wasn’t a “deal breaker” – it wasn’t a threat to our relationship.
- I was in charge of myself: would I change, how much, how quickly, in what direction, how far, etc?
Framed this way, Patty’s request was an invitation for me to be different – an invitation I could accept all of, parts of, or not at all.
And that made all the difference for me.
In that safety, I moved to curiosity, asking her more questions. We discussed why she felt this way and how it might benefit our working relationship. I even tried on this new posture, and rather liked it. I talked about my fears with it, and how others have reacted when I was “strong and focused.”
We both understood each other better, and our work is better because of it.
How might this apply to you?
Have you ever felt that someone’s “feedback” was actually a “mandate”?
Do you see a difference in your energy between receiving a “mandate” and an “invitation”?
How might you change your feedback so it feels more like an “invitation”?
5. The Blue Backpack
Finally, I want to show you an example of a “scaling question”, that is, a question where the answer is on a numeric scale. Let’s set the stage:
In your 1:1 with Tim, a Staff Engineer on your team, he mentions that it’s been a stressful month for him. Work, kids, travel, bills – a lot is going on in Tim’s life, and not all of it is pleasant.
You’d like to learn more in a way that affirms Tim and supports his strengths. So, you try out this scaling question: “On a scale from 1 to 5, where 1 is low and 5 is high, how well are you managing stress?”
Tim answers: “3.5”
How do you respond?
A Visual Aid
Here’s our question on a 5-point scale, and the green dot represents Tim’s answer of 3.5. The scale is split into two: the blue area below the dot, and the red area above the dot.
Typically, managers/consultants (and doctors) focus on the red area: the deficiencies. In fact, the usual way to look at the red area is “the distance we need to cover to close the gap”. Clearly, “the problem” is that Tim isn’t high enough on the scale, and, conceptualized that way, the manager’s job is to get Tim from 3.5 to 5. After all, wouldn’t it be better if Tim were at a 5?
This is so clear, in fact, that we never question it. If the scale goes to 5, and the current value is 3.5, then our job is to get up to 5.
Simple. And wrong.
Let me explain: the blue area, below the dot, represents Tim’s rating of his ability to manage stress right now. And Tim’s ability to manage stress is a culmination of Tim’s resources, strengths, relationships, biology, genetics, culture, education, mindset, skills, history, family, friends, experience with stress, and successes. Without any prompting or help, Tim is using all of those lessons and resources to manage his stress. Impressive stuff!
Said another way, the blue area represents the resources Tim is already using, and already knows how to use to cope.
Blue or Red
Again, the blue area represents all the resources Tim has to manage stress. Things he knows how to do, lessons he’s learned, people he can count on, etc. This is Tim’s backpack of tools he’s accumulated through his life’s travels.
And the red area represents… what? A lack of something? Ideas? Resources? Skill to use them? Drive? Awareness?
Managers are used to asking questions about the red area to “diagnose” such deficiencies. Questions like:
- Have you tried meditation or exercise?
- If you just focused, you could get these things off your plate, and then you’d feel better.
- You’re taking it too seriously; you just need to let it go.
- How much vacation time do you have left?
- What’s so stressful? Your life can’t be that hard.
Each of these questions infers that Tim is deficient, unaware, unmotivated, broken, or somehow not enough. Though that’s the way we’re used to attacking the problem (“head on”), in this case, science shows it doesn’t help. In fact, it typically makes the other person resistant to your ideas, and want to stop the conversation.
Think of the red area as the area to avoid. 🙁
Look in the (blue) backpack
The really interesting area to explore is the blue area, the resources Tim already is using and knows how to use. So, here’s how you start that conversation:
“How did you manage your stress so it’s all the way at 3.5?”
That question emphasizes that Tim is doing a lot to manage his stress, and asks to learn how he pulled off such an amazing feat.
Imagine you were watching someone free climb a 20-foot wall, and they had scaled 14 feet. Which is more encouraging:
- “Wow, you’re so high up! How did you do that?”
- “Why aren’t you at the top yet?”
Just like the rock climber, asking Tim how he managed his stress all the way to 3.5 invites him to reflect – and talk – about what’s working for him. It emphasizes what he already knows how to do and the resources he already has.
Because, frankly, Tim’s more likely to be able to do more of what he knows – and is working – than take your advice about something that worked for you. That means all your advice is pointless, meaningless, clueless – and usually unhelpful.
When Tim sees how far he’s come – 14 feet of the wall – and what resources he used to get there, he’s likely to do more of what’s working. That’s why asking “How did you make it so far?” is much more valuable and helpful than offering advice (“problem-solving”) on what you think Tim needs to do to get to your goal (a “5”).
And never forget, the 5 is your goal, not Tim’s. And the 5 is complete fiction – just a number on a scale. Tim might be perfectly happy where he is, and there is no “problem” that needs solving.
So, to recap, use a scaling question to:
- Ask how someone rates themselves on a numeric scale
- Celebrate how far they’ve come, and ask how they did it
- Listen. 🙂
That’s it – I promise deeper, more interesting conversations will take place.
Conclusion
In a world where people are being replaced with AI, more than ever, we can’t afford to act like robots.
It’s imperative that you connect authentically with those around you to build safe, effective, performing teams.
These five hacks are the tip of the iceberg for what’s possible, and I hope they inspire you to move beyond scripts, tap into your curiosity, and get to know others better.
Oh, and use these questions with care. They are powerful. Remember that you’re asking people to take a risk by being more vulnerable – so you should be prepared to do the same. Of course, you may find yourself sharing yourself in new, more profound ways, too. That can be scary, but people want to connect with their leaders before they trust them, so it’s table stakes.