If You Like Working With Someone, Should You Tell Them?

If TLDR, Here’s The Bottom Line:

  • A big fat resounding Yes.
  • Is there a chance you will regret it in the future? Possibly.
  • Might they misunderstand you? Probably.
  • Should you still do it? Undoubtedly.
  • Why? I’ll tell you why.

Why Didn’t You Tell Me?

A few years ago, I bumped into an old colleague. She was a vendor that worked with me when I was client-side. I loved working with her team. They were professional, friendly, creative, punctual, smart, and came sans the usual nose-in-the-air attitude that is often a non-negotiable attachment with creative agencies. (“You know nothing of the creative process you suited-booted loser client! Nothing!”)

As we caught up she told me she had dropped my brand as a client a few months after I left. “We hated doing your work and you paid us pittance.”

That was a punch to the gut. I had zero knowledge of that. Why didn’t they ever tell me? And if they hated it so much why did they stay so long? “Well, we liked working with you.”

Now you may think I chose this example to toot my own horn and tell you my vendor partners liked working with me, but it is quite the opposite. I felt like I had failed at my role if people who worked with me day in and day out, couldn’t even tell me they were unhappy until after I’d moved on (with a few pints aiding their courage).

Worst of all, why didn’t they ever tell me they liked working with me?!

On The Flipside, A Different Agency

At one of my client-side roles, we outsourced work to a social media agency for a brief period to test the waters. Their account manager churned almost every month, and the stress of having to go through brand briefs again and again began to take a toll on our relationship.

It didn’t seem worth the effort with both parties losing money and precious time. They did not like working with me. And that feeling took no time reaching their boss, and my boss. Several “we need to talk” sessions later, we parted ways, but not before my brands took some heat and damage, as did I, as did the agency’s account managers.

I Absolutely Do Not Like You One Bit

If your daily work interactions are with an average of say 10 people, you are bound to like working with some of them more than others. Pretend to be egalitarian in your love for your colleagues, and you just might fool everyone but yourself. Heck, even parents secretly have a favourite child (we will never speak of this ever again because we love you all equally forever!)


But as we have all experienced, not everyone pretends to like everyone. Some people are brutally vocal about not wanting to work with a colleague they don’t like and will spare no feelings in doing so. Just ask your HR Manager!

I Like You vs I Like Working With You

Since moving to a new country I’ve spoken to many a trailing spouse about how they build their social lives and make new friends. “We mostly just hang out with colleagues after work.”

If this is true of most of us, surely we must like our colleagues to want to spend even more time looking at their faces than we already do? And we must enjoy talking to them about work and sundry enough to also drag our partners into it? We must click with them on some (at least superficial) level to willingly spend our limited time on Earth in their company.

  • But can you like your colleague without liking working with them? Yes.
  • Other way round? Yes.
  • Like them and working with them? Yes.

So Should I Tell You?

I don’t know about you, but I cannot remember ever telling my best friend – hey, I like you. Mutual likeability is the keystone of friendship, yet it is seldom expressed.

So if you do like your colleague (we’re talking platonic friendship ‘like’ here, I have no idea what to do with any other kind of like, please talk to a therapist), you are in all probability not going to tell them that.

But if you like working with someone, should you tell them?

  • A big fat resounding Yes.
  • Is there a chance you will regret it in the future? Possibly.
  • Might they misunderstand you? Probably.
  • Should you still do it? Undoubtedly.
  • Why? I’ll tell you why.

Because People Like To Be Liked

We all want to be liked. We all want to be told we are liked. Some of us can list “need to be liked” as point one in the W column of our swot analysis.

If you like working with someone (because you are super productive together/you have each other’s back/you both care equally little about your jobs), you should tell them that.

Make their day.

Say – hey man, it’s really cool working with you. Nicely done on this project bro, I enjoyed putting it together with you.

Told the boss the project is delayed, but did it together and split the heat? Cheers mate, enjoy your weekend that I will not be spending with you.

Tell your boss and their boss you like working with them. Tell your other colleagues how cool they are. Write it on email. Use emojis. Try to be specific.

Because Then, You Put The Onus On Them.

When you are in receipt of whatever you consider “favourable” behaviour, making a solid expression of how pleased you are puts instant pressure on them to keep up that behaviour.

If you said to your boss – “I have respect for and like working with you because you don’t micromanage people” – how can they possibly ever do otherwise? If they also have a need to be liked (they do), it suddenly makes them very aware that their actions are being watched, and observed, and judged, and that they risk losing your liking if they alter their behaviour.

Open The Doors To Honesty

When we express things we like, it opens doors for us to honestly talk about things we don’t like, without being shut out.

Had my agency in the first example said to me: we hate the jobs you’re sending our way, and we’re not paid nearly enough to work around your brand’s restrictions – I would’ve instantly gone on the defence.

If they prefaced that with: we really like working with you, and we want to make this work – it would’ve put so much pressure on me, I would have fought with my boss to raise their retainer and done my best to make their work interesting.

Oh Hello, Vulnerability, Old Friend

We often hesitate to compliment our colleagues because:

a) we’re insecure monkeys.
b) we think it will go to their head if we praise them.
it makes us feel like we are now somehow below them, at their mercy. In other words, vulnerable.
d) we think they will go around telling people we like them, and that will make us look weak.

There is merit to all of these fears. It is for you to decide if you want to confront them.

What If I Stop Liking Working With Them?

After my encounter with the agency owner, I made it my mission to tell anyone I liked working with exactly that – every account manager, every client, every partner-freelancer. I like working with you, I love your attention to detail, I really like talking to you!

So what went wrong? Oh, a few things.

1. Misunderstandings: hey man, this is really cool, I enjoyed our conversation last evening! “Uhh. I’m not really interested.”


2. A change of heart: someone I told I really liked working with, I gradually stopped as I got to know them better. I found myself less and less attracted to their work actions: excessive capitalistic greed, detached communication, pendulating decisions, anti-feminism. All of it their prerogative! Despite possessing this newfound information judgement-free, I felt pretty silly for saying all the nice things I did, because now my interactions with them are increasingly objective, impersonal, walled-off.

To sum up, it may backfire, but we can all be kinder to each other at work anyway. If you like working with someone, but are afraid you may stop in the future, tell them anyway. There’s an 8% chance you’ll regret it, do it anyway.

By positively reinforcing work behaviours we like in our workplaces, we can all build healthier environments for each other!

Do you have a related work-story? Tell me here.