The Cost of Unmet Expectations

Yesterday, I found myself sitting across from a client — a CEO of a small company with a tight-knit leadership team of five people. Picture this: we’re sipping coffee, and he’s venting about his team. “There are a few leaders here who want to grow or take on new roles,” he starts, leaning in with that I-have-a-problem-but-I-don’t-want-to-say-it look.

Then he drops this gem: “I just don’t feel like… they’re there.”

But it was clear — he was wrestling with how to bridge the gap between where his team is and where they want to go.

— Intrigued?

So was I.

Let’s unpack this.

But before I continue, let me tell you why I am sharing this with you.

In the years I have been sitting with leaders to discuss processes, strategies, and better ways to create a healthy team culture, I’ve heard a similar thing every time. If you are in a leadership position — or on the other side — I think knowing and understanding both sides of the picture will help you lead those conversations better and better support, whether it’s your team or your leaders, to make a decision.

In a way, what I hope to accomplish with this post is to bring perspective to both sides, so you don’t lose a good employee or a good opportunity because expectations were only set from one side of the table.

So let’s continue…

After a few minutes of him explaining how these employees don’t have the experience or how he doesn’t think they will know how to do certain things, he shared that he doesn’t think “they” are ready.

So, I tried to understand his expectations — the expectations he has for each of “these employees”.

The problem with expectations is that they’re often based on an idea in your head of how things should be, but as a leader, you haven’t actually tested or clearly communicated that idea. To make it more complicated, these expectations can change over time — what you expect now might be very different from what you expected a week or a few months ago. The challenge is that you’re often figuring out and adjusting these expectations as you go, without realizing how much they’ve shifted.

Which makes those expectations unfair.

So we got to this point: “Expectations”.

I wanted to ask him a few questions to spark further thought outside of the “simulation” in his head:

• Is this employee resolute and does he/she have the attitude and commitment to the organization to be willing to learn and solve problems on the go?
• Have you previously mentioned what your expectations are and provided a career plan to support their growth, giving them opportunities to learn and practice some or most of those activities?
• Have you asked him/her what their expectations are, and are you responding to those expectations?

At the last question, he stopped and seemed to get into a more defensive mode. I asked again:

• Do you think you are responding to all their expectations as their manager?

After diving deeper into the conversation, I continued to ask questions:

• How do you think those gaps have affected their ability to grow and achieve your expectations?

Finally, I asked:

• Would you regret it if this employee left tomorrow because you didn’t meet their expectations?

As leaders and employees, it’s very easy to think about our expectations as if they were set in stone and only existed in our minds. Guess what? On the other side of that conversation, the other person also has expectations, and in most cases, you haven’t met their expectations either.

Imagine an employee could tell you, “You are not ready for the role,” because you haven’t met their expectations as a manager.

Wait.

I know.

But I’m trying to offer a perspective that is more holistic. When you consider your expectations, consider what expectations the other person has of you and how you’ve failed them — especially for those employees who are proactive, bring a positive attitude to work, don’t work to grow their egos, and positively affect progress.

So what now?

There is no recipe for this. For me, when an employee brings a conversation to you to talk about salary and growth, you are probably too late if you haven’t proactively started that conversation yourself. My guess is that they could be out the door in no time if they don’t see anything changing.

As a leader, you can choose to provide a growth path or not. Of course, the company will have certain limits, but the decision, after all, is whether that employee is worth investing in and how you can support them to get closer to where they want to be.

To do this, it’s key that as a leader you leave your ego aside and ask yourself how you’ve failed them and what you could do better. Use those learnings to improve, but also don’t be afraid to ask them what expectations they have of you and how they think you can support them.

A leader who thinks that their employees’ success depends solely on their effort is very likely living in a “simulation.” Leadership is very much about supporting, enabling, and empowering. For that, leaders must focus a big part of their time on doing that for their teams.

To be fair, I know from personal experience that leaders are often doing 200 things a day, often left with very little time to actually “nurture and support their teams.” Something is broken in the way work and leadership are organized.

So what are the things that should be highlighted by leaders?

Hello Leaders!

• Approach career growth and build career plans with your teams proactively. Avoid waiting until they ask you about it.
• You are not the only one with “unmet expectations.” Learn about what your employees expect from you.
• If someone has requested a growth plan, act quickly (it’s already too late). They could have an offer waiting or start looking for a job and leave before you even make a decision (I’ve seen this so many times).
• Learn from what your employees expect from you. You will be a better leader for it, and I promise it can bring a lot of joy and fulfillment if you do. Don’t worry — the road is infinite, so if you are a life-long learner, this is the perfect journey for you.
• Request and block time on a weekly basis to think about your team and how you can support them.

Make sure each team member has a career growth plan. Make sure you provide opportunities to grow, learn, and experiment. Stay aware of new trends in leadership to better support your team. Provide feedback, create safe environments, and lead by example.

Hello Teams!

Now, if you are someone asking for a raise or a change in your career, what can you learn from this?

• Clearly define what you need to succeed.
• Share your expectations too.
• Try to understand what you can expect as soon as you start working at a company and identify when certain expectations are unattainable in your workplace. If that is the case, focus on how you can get the support you need to learn and get experience in the areas that could help you achieve those expectations in the future.

In a way, the takeaway is that expectations exist on both sides of the table, and by only hearing what a manager expects, the full picture of this working relationship remains incomplete.

Let me share a personal story.

Not long ago, I lost an incredible employee at a company I support. She was smart, dedicated, and brought so much value to the team. But one day, she decided to go back to her previous company.

I saw the signs — she needed more flexibility, and she was exploring opportunities for better compensation. I even had a plan in mind to address these things, but here’s the truth: I didn’t act fast enough. As a company, we weren’t prepared to adapt to her expectations, and another organization offered her what we couldn’t at the time.

That loss hit me hard. Since then, I’ve been pushing myself to get more involved with the HR team, diving into discussions about our company benefits, flexibility policies, and salaries. It’s become clear to me that as a leader, I can’t expect to keep great talent unless these things are clearly defined at the company level. It’s not just about having a plan — it’s about acting on it before it’s too late.

It was a tough lesson, but one I won’t forget.

But…

Here are a few things you can take away if they serve you…

To wrap up, I’d love to hear your thoughts:

• Have you experienced something similar in your organization, either as a leader or an employee?
• What strategies have you seen work to align expectations and retain great talent?
• If you’ve been on the receiving end of unmet expectations, what would you have wanted your manager or company to do differently?

Let’s turn this into a conversation!

Share your experiences, insights, or even challenges in the comments below — your perspective could help others navigate this complex but crucial topic. 😊