Difficult Conversations at Work: Why Tech Leaders Struggle


Corry Robertson, PCC profile picture

By: Corry Robertson, PCC

woman having difficult conversation

Last week I wrote about Debugging Leadership in the Tech World where I shared some ideas about breaking unspoken workplace rules so that you and your team can have real conversations.

I suggested that you carve out time for difficult conversations to emerge, honour the kind of bravery it takes to say what needs to be said and then reward those who show the courage to trust you and each other.  

When you read that post did you think that I was asking for the impossible? If you did, you wouldn’t be alone.

What makes holding real conversations extra difficult for people in tech?

A Harvard Business Review article entitled Leaders Need Different Skills to Thrive in Tech says that conversations are tough because of the consistent ambiguity of the workday.

Tech employees have to navigate unclear, overlapping and shared accountabilities that can create confusion, misalignment and competition. In addition, these priorities, projects and assignments constantly shift.” (Grenny & Maxfield 2016) 

Case in point, last week I was working with a VP HR who had recently joined the firm from another industry and this very issue came up in our conversation. 

Not only was he new to tech and to the company, the company had never had a VP of HR before.

Being from another industry, he was shocked at how slow and inefficient the workflow was because of those very facts described by HBR. 

Every question he was asking was getting responses like:

  • I don’t know, that’s not my job.
  • I don’t know, that’s not my department.
  • That task wasn’t part of my assignment
  • I don’t know who is working on that – but it’s not me.

When he asked who to go talk to, fingers either pointed in half a dozen different directions or shoulders simply shrugged.

The scenario that the VP of HR described indicates that disengagement is already a problem at that company.

Luckily for them he spotted it right away and knows how to correct it. The big question is, will the big bosses buy into the solution? 

Why decision-makers need to buy-in.

When employees have to cope with unclear, overlapping and shared accountability it creates a work culture where there’s a great deal of confusion, misalignment and finger-pointing. 

This is the root of interpersonal conflict, when trust breaks down and quiet chaos starts to unfold. 

I call it “quiet chaos” because you may not see it happening but it’s powerful and destructive to your company.

Competition rather than collaboration occurs when people guard their time, their turf and their resources because they don’t want the workday to get any harder than it already is.

This is stressful, frustrating, exhausting and before long employees come to resent the company so they either disengage, quit and leave or quit and stay.

If they stay, they put their heads down and do the minimum needed to get through the workday with as little stress as possible.

What do real and even difficult conversations accomplish? 

Difficult conversations create the transparency needed to hold everyone accountable. 

In this context, accountability means that everyone is following through on their commitments and changes are communicated. Icebergs are avoided way before the risk of hitting them is real because everyone is allowed to speak up and say the unpopular thing.

I can hear you now. “Corry, my door is always open! I encourage people to come and talk to me! I’m totally transparent.”

I believe you mean that, and I’m sure you practice that. 

But here is what’s ALSO true: when you start seeing signs of disengagement, I can tell you without a doubt that your intention to be open and transparent is not having the effect you think it is.

Looking at yourself in the mirror is a hard thing to do, but courageous leaders understand it’s a necessary step.

Then we can go deeper and look at HOW to communicate effectively and hold each other accountable.

Ultimately successful cultures of today’s tech world require that all people are expected to be leaders, regardless of rank, role or number of people who report to them, even when that number is zero.

Just telling employees that you expect them to behave like leaders is not enough. 

You need to be in control of the culture at your company which means being explicit and consistent about what you mean. 

Your employees need to be taught how to follow through on your expectations. 

There needs to be tangible and intangible rewards for living up to your culture standards and consequences for failing to do so.

For a concept like mutual accountability to work, employees need to work on skills like how to establish their leadership presence,  and how to give and receive constructive feedback

In addition, they need to know how to use communication models that clearly document who is responsible and accountable, who needs to be consulted and informed and what extra support may be needed during the project life cycle.

And that’s where leadership coaching comes in. 

To manage progress in a way that strikes the right balance between directing and empowering, managers need to use a coaching methodology for delegation and workload management like what I teach at The Coaching Academy for Leaders.

The tech world is fast-paced and constantly reinventing itself. The pace of change today is unprecedented and difficult for people to cope with, even for the most experienced and brilliant leader.

The good news is, although the world around us is changing, human beings and the skill sets that help us to thrive remain the same. 

Leadership principles are timeless, ageless, genderless and borderless so once you understand them, you’ll have that powerful wisdom forever. 

Coaching is the ‘how-to” skill set for putting leadership theory into action and more good news….it works and it can be learned.

Who’s in?


Submit a Comment

Your email address will not be published. Required fields are marked *

How To Become A Certified Coach

FREE GUIDE – Updated for 2024!

How To Become A Certified Coach in 2024:  Choose The Right Coach Training Program For You

Download and get immediate access!

Corry Robertson, PCC profile picture

Corry Robertson

Sought-after coaching culture expert, Corry Robertson has been helping leaders uplevel employee retention and performance for over 20 years.

Download Our FREE GUIDE
How To Become A Certified Coach in 2024 - Essential ICF Updates and Changes

Get Immediate Access

YES - it's on its way! Check your inbox for your FREE GUIDE. If you don't see it within 5 minutes, please check your spam folder and remember to White List our email so you can receive more leadership insights from us.

Get A Print-Friendly PDF Version Of This Article

Easily save this article to share or read later by downloading a print-friendly PDF.

Success! Check your inbox - it's on its way!

Share This

Share This Article!

Enjoyed this article? Share with your network and continue the conversation about leadership and work culture.