Why difficult conversations keep getting escalated to VP Operations – and what helps rising leaders handle them earlier.
If issues keep landing on your desk that you know could have been avoided if a project manager had just had a difficult conversation earlier, the real issue may not be communication skills. It may be leadership capacity.
There are unfortunately lots of examples:
- An attendance issue that hasn’t been addressed and creates overtime costs.
- A long overdue invoice that a project manager hasn’t followed up on pushes into the line of credit.
- A vendor stops submitting because they never heard back on the previous bid.
The initial difficult conversation itself may have needed less than 15 minutes, and didn’t need to be perfect. But the longer it’s avoided, an ever-growing amount of operational energy accumulates around it.
Waiting becomes an operational problem
One of the things I’ve noticed while coaching construction leaders is that the project manager usually knows the conversation needs to happen. They may even know roughly what they need to say.
But something gets in the way:
- “Maybe I’m making too much of this.”
- “I’ll give them one more chance.”
- “I don’t want to damage the relationship.”
- “I can’t risk today’s deadline to focus my attention on something else.”
- “I just want to check one more thing before I reach out.”
These hesitations are understandable.
Leadership involves judgment, relationships, authority, and competing priorities.
And it is uncomfortable using a different kind of influence – one that doesn’t come from being a technical expert.
But the operational consequences of waiting don’t disappear, they compound.
Consider an attendance issue: A PM doesn’t address it. Other employees notice. Resentment grows, work gets prioritized inconsistently, overtime increases, and people become overwhelmed. Eventually, quality suffers – which costs time and money.
Or consider an overdue invoice: The PM doesn’t want to push the client relationship. Revenue is delayed. Pressure on the corporate line of credit increases. What started as “they’ll pay when they can” becomes weakened trust – and eventually the conversation may be about penalties rather than simply understanding the payment process.
What’s hindering project managers in these situations
Rising leaders are developing their leadership skills in a different environment from the one many experienced construction leaders developed in.
Today, project managers are being asked to manage remotely, and to influence others without constant physical presence. Communication methods are quicker, choppier, and more and more asynchronous – email, texting, video calls, online submissions, automatic responses. The transactional elements of the work are happening much faster, but time for the relational elements is shrinking.
There are fewer moments to watch an experienced leader handle conflict, or to overhear a difficult conversation happening, or to be part of a sidebar about a misunderstanding after a trailer meeting.
None of that means today’s rising leaders are less capable.
It may simply mean that some leadership capabilities need to be developed more intentionally now.
How leadership coaching helps
When a PM keeps delaying difficult conversations, it’s tempting to conclude that they simply need better communication skills, and therefore a training course to expand their knowledge.
Another option is to pair them with a mentor – someone who can share their own experiences with difficult conversations for the PM to learn from.
But there’s also leadership coaching. Coaching guides the PM to examine what is getting in the way of putting what they know into action. For difficult conversations, the PM would explore what they are observing versus assuming, what kind of authority they’re comfortable and not comfortable using at this stage of their career, what outcomes they want from the conversation, and what would help them prepare.
Then the PM would have a difficult conversation.
Then they’d explore with their coach what happened, what to consider next time, and what they discovered about themselves.
The goal isn’t one successful difficult conversation.
It’s helping the rising leader become more willing and able to recognize, prepare for, and act on the next one.
That’s a different kind of return.
The return is operational capacity
The return on leadership coaching isn’t necessarily visible as a new skill on a competency checklist.
It’s the shifts you may miss if you don’t look for them – when a project manager handles an issue before it can escalate. When an invoice gets addressed before its overdue. When a relationship gets repaired rather than quietly deteriorating. When a project team regularly reaches out to each other.
That’s leadership capacity.
A question for you
What is the cost to your organization because one of your rising leaders hasn’t had a difficult conversation yet?
If you’d like to explore one situation, let’s have a short chat to consider what’s underneath the pattern and what might help your project manager approach difficult conversations sooner.
