Effective Strategies for Addressing Challenges with Senior Colleagues at Work
“Once I addressed the elephant, we were able to kick him out of the room."
- Sheryl Sandberg, American technology executive, philanthropist, and writer
Sheryl Sandberg is right — Nobody likes an elephant in the room, and the only way to get rid of it is to talk about the problem at hand.
In fact, good communication lies at the heart of addressing any challenge at work. In fact, unclear communication is the number one cause of unnecessary conflict at work! And when it comes to senior colleagues who don’t necessarily “speak your generation’s language”, this has never been more important.
As with any job, though, navigating the politics of workplace dynamics and individual relationships can be tricky! I’ve certainly been there (we all have!), but with the right mindset and approach, these conversations can become opportunities for growth, collaboration, and respect.
So, whether you’re managing up, managing across, sharing feedback, or just trying to smooth things over, here are six tried-and-tested tactics for handling challenges with your peers and senior colleagues.
1. Be in the right mindset
We’ve all had moments when we jump into a conversation guns blazing, only to realize afterward that we weren’t in the best headspace. What’s the lesson? Don’t even think about addressing a situation if you’re feeling defensive or angry.
For me, taking a breather before diving into a tough conversation with a senior colleague is the key. Before you chat, you should ask yourself these questions to make sure you’re in the right mindset:
Am I feeling angry, frustrated, or defensive?
Do I feel calm and open-minded?
Do I want to blame?
If yes, what can I do to neutralize it?
Is this the right time to have a difficult conversation or is there a better time?
Given our different strengths and blind spots, what could be causing our misunderstanding?
Amy Chan, of Renew Bootcamps, asks you to question: are you going into the conversation with a handshake (wanting to proactively and respectfully resolve things) or with boxing gloves (ready to get your way no matter what)?
While difficult conversations require you to take stock in your own mental wellbeing, they also require you to factor in your senior colleague’s headspace.
In my previous career, I remember having to pause before confronting someone who’d shot down my idea in a meeting. Instead of barreling in with frustration, I stepped back and considered their pressure and perspective. That mental reset completely shifted how I approached the conversation — and surprise! It was way more productive.
To sum up — As you ask yourself about your own mental capacity for a tough talk, also ask yourself this question: “Can I imagine what it’s like to be in their shoes now?”
2. Be a conscious leader
Another framework that can help you get into the right mindset is to ask yourself: “Where am I?” Figuratively, we mean.
The principles of conscious leadership ask us to consider:
Am I willing to be wrong or do I just want to be right?
Am I open-minded or close-minded?
Am I being reactive or curious?
Learn how to locate yourself and how to consciously lead with trust versus threat.
3. Start with an opener
Nobody likes to be blindsided. Ever. To mitigate this, difficult workplace conversations require a bit of “optics management” — Instead of opening with the problem, take a softer approach and try to take the edge off of what’s about to take place.
Personally, I’ve found that simple, low-stakes questions work great. Something like, “Is this a good time to chat?” goes a long way in giving your senior colleague a heads-up without triggering defenses.
And don’t undermine the classic “how are you doing?” or “what are your roses and thorns?”. Taking a few minutes to understand where your peer is coming from will help you establish trust and rapport from the start. Check out our trust-building questions.
Here are a few other soft openings to try:
“I’d love to ask you a question. Is this a good time?”
“I’d love to share an observation about last week. Want to chat?”
“I wanted to follow up on our conversation from last week. Got a minute to chat?”
4. Ask questions and lead with curiosity (before sharing your side)
When tensions are high, our instinct is to jump in with our side of the story and defend our position. I can tell you from experience, this immediate “fight or flight” response never ends well.
Instead, try to remain open and curious as you talk through your challenge.
As the famous saying goes, “there is no cure for curiosity" — because there doesn’t need to be.
Seeking to genuinely understand where your colleague is coming from will always be a winning approach.
It’s important you make your colleague feel heard, too, so try to genuinely understand where they’re coming from before you give your version of the story.
To give you an example: I remember once when I read a group email from my boss (and older person!), and I felt it was unnecessarily harsh towards me and my reputation. Instead of reactively firing off a response in the heat of the moment, I instead asked in a private email, “Hey, I wanted to chat about your message the other day. How did you intend it? I’d love to understand where you are coming from.”
Asking this question did two things: It led to a productive conversation that clarified a lot for me, and it helped both of us save face in a group email chain, instead of us calling each other out. In reality, I realized it wasn’t about me at all, it was about the stress they were under.
Ultimately, this honest (and difficult) conversation strengthened our relationship and created a more productive, collaborative, and honest work dynamic that made us both happier at work!
Remember: Even a little bit of curiosity can open up a lot of understanding.
Here are a few more questions to consider asking that will help you as you navigate the initial steps of what could become a tough conversation:
“Hey, let’s chat about last week. Clearly there was a misunderstanding. When [situation], I interpreted the message as disrespectful and short. I’m worried because this can create a tense atmosphere. What was your interpretation of what happened?”
“Listen, I wanted to discuss the Slack message the other day. Honestly, it stung a bit. I know we're both under pressure, and I know sometimes that can come out in our communication. How did you interpret it?”
“I know things rubbed you the wrong way last week. My intention was not to make assumptions. When you said [specific comment], it came across as dismissive. What’s your perspective on this?”
5. Validate their experience
I said this above, but I’m going to say it again — everyone just wants to feel heard. (Emphasis on the word “feel”.)
And this isn’t just a gut feeling. There’s research behind it! According to one study, invalidated people feel worse, less psychologically safe, less engaged, and have higher heart rates than those who were validated after completing a challenging assignment.
According to psychologist Marsha Linehan, validation means communicating to someone that their “responses make sense and are understandable within her [or his] current life context or situation."
Validating someone’s experience doesn’t mean you have to agree with them; it just means you’re acknowledging their perspective. This can be as simple as saying:
“I totally understand why you felt that way.”
“It totally makes sense why you feel that way.”
“Your perspective and reactions are totally understandable.”
“I understand why you see things that way.”
Imagine this: you’re in a meeting, tensions are rising, and someone feels like their input is being ignored. They might react defensively, or worse, shut down completely. And instead of launching into my counterpoints or trying to smooth things over prematurely, I’ll instead say something like, “I totally get why you felt sidelined during that discussion.”
The moment this person feels seen, the entire energy of the conversation can shift. It’s like hitting a reset button!
Here are two communication exercises to try the next time you’re facing a challenging conversation:
Mirror and summarize
Try this:
“So it sounds like you felt…. Did I get that right?”
“If I got that right, I think you said… is that right?”
Ask more questions
Or this…
“I’m curious to learn more [something they said]...”
“Would you mind telling me more?”
6. Focus on the impact, request, and explain expectations
The next step after you’ve listened and validated your senior colleague is to focus on the impact this has had and set clear expectations for the future.
A few years ago (at my previous marketing job), I had to address a senior colleague’s abrupt communication style that was affecting team morale. After listening to their side, I explained how their tone in meetings was impacting the team’s motivation.
Instead of attacking them, I focused on the outcome I wanted (I wanted a more supportive environment!).
Remember: giving feedback without a clear request is a complaint!
Then, I asked for their thoughts on how we could work together to make that happen. Here are a few example talking points I explored at the time:
“I know you prefer to be more blunt and direct. I prefer that we call each other out in private vs publicly. I’d love to discuss how we can improve our communication styles to support our team better. Any ideas?”
“I believe in respectful and constructive communication because it fosters a positive work environment and drives team success. What do you think about how we, as leaders, can best handle things if a disagreement comes up in the future?"
“I totally understand that you prefer a more direct approach, but we need to find a balance that aligns with our company values and supports our team. What do you think?”
Engaging your senior colleagues in the solution like this often leads to more buy-in and a better outcome for everyone.
Finally, share how much you value their contribution, loyalty, and skills
Ending a conversation on a positive note is non-negotiable. Even if it’s been a tough talk, it’s important to reinforce that you value your senior colleague’s contributions. After a difficult conversation with a senior colleague, for instance, I always try to make sure I say something like, “I appreciate your candor, and I know how much you care about the company’s success. Thanks for working through this with me.”
A little appreciation goes a long way towards building healthier working relationships! To quote Maya Angelou:
“I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
You’ve got this!
To learn more about how Reframed Coaching can help you gain the confidence you need to succeed in difficult conversations at work, explore our 1:1 and group leadership coaching or, if you’re a new startup manager, join our Startup Manager Training Cohort!