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How To Provide Critical Feedback Without Being Afraid To Upset a Colleague?

Updated: Sep 28, 2022

Have you ever been in a situation at your workplace where you felt compelled to withhold your feedback not to upset another colleague? In this blog, the author shares a story of needing to give someone feedback and reasons for withholding it at the moment for the sake of not upsetting that critical employee. The blog also includes opinions and thoughts from a few other people as well as lessons learned from the experience.


Being a boss at your own company has its advantages but also poses unique challenges when you have important employees who are responsible for important tasks, and you find yourself in disagreement with something they do or say.

I was talking to our “right-hand” employee at the company (let's refer to her as Susan going forward for easy reference) about different topics and issues. She has been working with us for many years and has been involved in numerous important projects and tasks throughout all this time. Susan “wears” many hats at the company and is involved in numerous important aspects of the business. One of the topics we started discussing was financial billing, its cycles, and all the issues we had with it at the time of our conversation.

Susan started complaining to me that the person responsible for hiring new employees hasn’t hired another experienced biller to help with the process. There is another side to that story, but I will come back to it soon. It’s worth noting that Susan loves to be in charge and show how important she is to the company. Therefore, she works best with billers who come to her for suggestions and who could be just told what to do. At the same time, they are not making their own decisions when problems arise. Instead, they ask Susan for help which distracts her from other important tasks. Therefore, she often expresses her desire to work with competent, knowledgeable, and self-reliable people who can make important decisions without constantly involving her. However, she struggles to share the top spot with others.


I shared the story with some of my writing colleagues and they offered several interesting opinions and thoughts.

Luba shared an insightful view from the corporate world: “I have seen this scenario many times. Leaders are afraid to let go but at the same time, they are stretched so thin, they are either impossible to get a hold off to remove an impediment, burn out quickly, or complain that they are overworked. When you offer help, they say, “Oh don’t worry, I got it!” or they will say they have no one reliable enough to delegate the work to. When you dig deeper, in some cases they are afraid to let go because they are not sure what they will do themselves.”

I personally might add that someone like Susan would want to show herself and others that she is capable of multitasking and still producing great results. She often needs help because of her projects’ scope but prefers to do the work herself or delegate manual tasks to those who don’t question her decisions.

Diana offered another thought-provoking insight, which rings true for small business owners: “In my opinion – this is the fear of judgment stepping in. A conversation with Susan should take place about her understanding of her role, of outlining goals and expectations, as well as the discussion about team interactions. If she is the right person for the job, i.e., someone who wants the company to succeed, who understands what value she and others bring, and is cognizant of her capabilities and time constraints with all the hats she "wears", she should be willing to let go of control. It’s super tricky to have these conversations with key players, as the fear of losing them is so high, but on the other hand, it is the growth of your joint baby, i.e., your company, which cannot happen without people truly willing to relinquish control.”

As a small business owner, you often must make a choice regarding which battles to fight, and which ones to let go of at any given moment. You can’t fight them all. Importantly, a lot depends on the employees’ personalities and how easily or not they accept constructive criticism. Some people only go on the defensive and don’t see the reason or recognize an opportunity to learn from their mistakes. However, if they also make many correct decisions for the company, as an owner you may show some leniency towards shortcomings and mistakes to retain that important employee.

Viktorija offered several probing open questions to ask: “Susan, what would you do being a boss? Do you think a new person should be able to make decisions? What would help Susan to concentrate on her tasks and to let a new person implement their vision?”

I see a benefit to this approach. Asking employees to imagine what they would do in a current difficult situation allows them to be in control and think outside the box. It allows them to see the situation from a different point of view, and they might make more educated and thoughtful decisions.


I agreed with Susan at that moment but in reality, we had already hired a few very experienced billers. Unfortunately, Susan was disagreeing with them over who should make what decisions and was complaining about one of the biller’s lack of socializing with other team members. I went along with Susan’s view on the issue not to upset her and to avoid tension. At that moment I chose not to put part of the blame back on her for the fact that we didn’t have another experienced biller at the company. By not contradicting, I allowed Susan to remove all the blame and responsibility from herself and place it on the person in charge of hiring new employees. She left the meeting considering herself correct, without realizing the problems she has been causing for the billing cycles and in turn for the company.


There were several lessons learned from that situation:

1. It is imperative to the company’s success to address both positive and negative aspects of key employees and processes to easier fix or address the existing issues.

2. To analyze crucial conversions with key employees in a timely manner and come back to important issues that were not discussed or addressed during the conversion. Not to sweep things under the rug but address them head-on and come up with possible solutions.

3. Choose your battles. Not every issue is worth fighting for. Know the personalities of your key employees who greatly contribute to the company’s success, and know where to push the issue forward and where to let it go.

4. Work with the strengths of your employees, and assign tasks that they can complete successfully.

During my initial conversation with Susan, I should have mentioned the fact that we did hire some experienced billers before that didn’t work out for Susan. I should have also asked her to imagine the scenario where she can easily hire the biller of her dreams and describe all the necessary qualifications and then analyze how realistic those qualifications are. I would also ask Susan what kind of people she prefers to work with and brainstorm how realistic it would be to find such people. Analyzing a situation from another point of view can do wonders!

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