Have you ever experienced a professional conversation that didn’t feel right? Did you receive a direction that made you squirm in your chair?  Have you ever witnessed a situation where a colleague’s or leader’s behavior made you uncomfortable?

If so, you may have considered your options and the risks that speaking up may represent.

Throughout my time in the world’s largest logistics company, I stood many times in front of the decision: To speak up or not to speak up.

I believe that if you become aware of something risky or limiting to an organization, team, or individual, you have the responsibility to engage. Otherwise, you are becoming a part of the problem.

As a result of this belief, I repeatedly represented the team’s voice about crucial issues with an organization-wide impact. I shared my observations and insights about executive-level dynamics that could have limited or disrupted my career.

Despite considerable discomfort, I chose to engage. I was well prepared and clear about the right thing to do, but I was undoubtedly nervous.

uncomfortable conversation

Taking on these uncomfortable conversations did not make for a smooth ride. In the short term, my position brought a lot of uncertainty. At times, I felt like a whistleblower.

In the long-term however, the leadership team that I worked with appreciated me speaking out. The big perspective, where individual needs are superseded by the greater good of organization, has proven my actions helpful.

This, you may argue, is not always the outcome of speaking up.

I agree. Maybe you are not lucky to work with open-minded leaders or the risks linked to a difficult conversation are such that you seemingly can’t engage.

Still, it is critical to speak up.


Because if you don’t, your integrity is at risk.

You can replace a job. You can replace a leader. But you can never replace your integrity.

If you are wrong, you can always apologize. If you are right and things don’t take a favorable course of action, you can prepare to deal with it.

In both instances, however, you won’t have to regret that you shied away from what you perceived was right.  Undoubtedly you will learn from the experience and move forward.

Also consider this:

Whom do you believe people will see as an inspiring leader worth following? Someone who chooses to go with the flow? Or the person who stands up for the right thing?

In my practice, it is refreshing to see that more people are ready to immediately speak up for fairness, inclusion, or ethics these days.

Suppose you are considering speaking up regarding a subject with an organization-wide impact and/or executive-level attention. In that case, you may consider taking it slower and preparing.

These steps have proven valuable in my experience:

1. Ensure you act out of the right motivation

Reflect. Ask yourself: What’s my ultimate motivation for engaging?

If the primary reasons are ego-driven, meaning it is about gaining an advantage for yourself or your team, scratch it. There may be another, more respectful way of reaching your goals.

If you feel basic principles are in the game, such as ethics, fairness, and the greater good, then go ahead! Such motivation will carry you over discomfort, potential consequences, and doubt.

2. Review all the risks your action could bring

What are the risks?

Who else may be impacted if the risks materialize?

Can you mitigate the risks ahead of time? How?

What’s the worst possible outcome?

Can you live with it?

3. Gain perspective

Discuss your topic with unrelated parties. Whether it is your significant other or an industry expert, getting an external view may bring a different perspective and reassurance.

4. Create alliances 

Is there anyone who shares your observations and concerns?

What’s the view of the influencers in your organization?

What’s the likelihood they’d be open to supporting your case?

Speak beforehand with some of leaders or executives to gain powerful allies supporting your case and possibly mitigate any risks.

5. Don’t dwell on the outcome

The outcome doesn’t define whether you spoke up successfully. There are multiple factors in the game – many of them are not within your scope of influence.

Have you done your best to prepare for those elements you can influence? Was your delivery factual, driven by higher principles, and delivered with impact?

If yes, you were successful. You’ve done justice to your responsibility. The next step is to observe the dynamics unfolding, reflect and learn.

Whether you’ll evaluate the further development as “favorable” or not, there will be valuable information that will catapult your growth and self-respect.

Effective leadership starts with facing uncomfortable conversations. 

Do you have a difficult conversation that you need to prepare for?

Get in touch. I’d love to be of service.

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