Terry Boyle McDougall: Giving Feedback; How To Be Honest Without Being Hurtful

A leader’s success is predicated on the success of the people on her team. As one of my mentors used to say, “Your team members are either going to be part of your success or part of your failure. You decide which.” A leader’s role is to set the agenda for what the team will work on and keep the team moving with pace toward that goal. If there is disagreement or misunderstanding between the expectations of the leader and the activities of the team members, the goal will not be achieved as efficiently as it would be otherwise. Feedback is what keeps the activities and the expectations aligned.


As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing Terry Boyle McDougall.

Terry Boyle McDougall is an Executive Coach and CEO of Terry B. McDougall Coaching. She helps high-achieving professionals tap into their full potential so they can enjoy more success and satisfaction in their lives and careers. Before becoming a coach, Terry was a long-time corporate marketing executive where she led teams, developed strategies and advised senior leaders to drive business results. She is the author of Winning the Game of Work: Career Happiness and Success on Your Own Terms.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Iworked for many years as a marketing leader in two large banks before leaving the corporate world in 2017 to become a coach. When I graduated from college, I entered the workplace as an ambitious “go-getter” and it didn’t take long for me to recognize that it would take more than just brains, talent and hard work to get ahead. From the beginning of my career, I was a student of the “game of work” and I have always been fascinated about how to influence and make a meaningful impact at work. I’ve read widely on the topic of leadership and workplace effectiveness — lots of books as well as thought leadership from the top business schools and consulting firms.

There were a couple of points in my career that I made some big decisions that helped advance my career. When I’d been working for a few years, my best friend at work got married and moved away. It woke me up to the fact that I needed to be in control of my own destiny at work and that if I just floated along without steering my ship, I’d probably end up in a place that I wasn’t necessarily happy with. I decided within a couple of days of her leaving to quit my job and go back to business school full time. This was May and by August I was enrolled in a full-time MBA program.

I didn’t know how I was going to pay for it, but I believed that this would be an important thing for me to do if I wanted to advance in my career. The lesson I learned is that sometimes you have to put your foot on the path and start walking before you can see what’s needed to achieve your goal. In this case, once I was accepted to the program, I was able to get an on-campus job and an assistantship which helped me pay for my MBA. Had I waited to see how I would pay for it before I took action, it would probably still be a pipe dream. Though it was a bit of a snap decision, going back to school full-time was one of the best career decisions I ever made.

As a leader, I relished coaching and mentoring my team members. I realized that I had perspective about work that was a little different than many and that I was able to help people understand and value their contribution in the workplace more. I decided to become a full-time coach because I recognized that there was a need for someone who had been in the corporate trenches to help high-achieving professionals have more impact with less stress. I’m all about helping people maximize the overlap of professional success and personal happiness. So many lessons I had to learn the hard way and it’s satisfying to me to help people avoid some of the pitfalls I fell into in my career.

What do you think makes your company stand out? Can you share a story?

I have a perspective that it’s important to always remain focused on the impact that one has at work rather than on how hard you work. Being someone who has very high expectations myself both at work and at home as a wife and mother, I know the mindset of the overachiever and I also know the cost of being so goal oriented that one can lose sight of what’s important.

I decided to write my book Winning the Game of Work: Career Happiness and Success on Your Own Terms to share my insights on how to be strategic in the contract between employers and employees. I try to live the lessons that I share with my clients. I try to show up authentically in my own work and encourage my clients to allow themselves to be seen at work as well. I am pretty active in the print media, on podcasts and as a speaker sharing my message of showing up authentically.

When people ask me about what coaches do, I like to share this saying, “It’s hard to read the label from inside the bottle.” As a coach, my job is to reflect back to people how they are showing up and through this reflection they can decide whether their behavior is serving them. Much like my clients, I’m also in the bottle and I can’t read my own label. I have to just notice how people respond to me and how what I do feels to me. Honestly, it’s hard to see clearly how I differentiate my company beyond just showing up in a way that feels real. I’m connecting with a lot of people that I enjoy working with and who are getting the results they desire, so I guess what I’m doing is working.

Can you share the most interesting story that happened to you since you started your career?

I have an observation and it is that when you say “yes” good things happen. Every time I have an interesting opportunity come to me, I can usually trace it back to a chance that I took or a time that I said “yes.” It can be very easy to try to protect yourself from the “what ifs.” We never know if a decision we make will result in the expected outcome, but I’ve found that even questionable decisions can result in great outcomes.

For example, shortly after I got my coaching certification, I enrolled in a business coaching program that cost a lot of money. I felt like I needed guidance on how to structure and run my business in a way that would be profitable so I signed up for this program with a coach who promised a lot for the investment. On the face of it, the program did not deliver on many of the things that he promised.

Even so, I cannot say that I made a mistake in investing in the program for a couple reasons. I met some great people some of whom I interviewed for my book. Secondly, I got a lot of benefits that were not promised. I believe that the investment that I made in the program was actually an investment in myself and the belief that I could build a profitable business, and I have done that. Though that investment didn’t pay off in the way I anticipated, it was a very important step in my progress to get to where I am today.

Very often we can look back and regret decisions we’ve made, but the reality is that we’d be in a different place today if we had made different decisions in the past. It doesn’t pay to have regrets. We’re always making the best decisions we can at any moment given what we know at that time.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This story wasn’t really funny at the time, but it is an amazing story about how opportunities present themselves when you prepare. After I’d been working for about 8 years as a senior marketing manager for a large bank, my boss left. He had relied on me as his right-hand person, often asking for my insights on the marketing strategy for the division. In the months after he left, I stepped up to informally lead the department. When the CMO decided to post the role, I applied and easily made it past the HR screening interview, but the next interview was a panel interview. I’d never taken part in a panel interview and I didn’t get myself in the right headspace prior to the interview. I ended up doing terribly. I was very nervous and allowed my nerves to get in the way of showcasing my abilities. I was eliminated from the recruiting process which was embarrassing and, frankly, devastating.

I hired a Career Coach to help me with my confidence and interview skills. As it turns out the person who the company ultimately offered the job to turned it down. The CMO decided to restart the interview process from scratch. I reapplied, bought some nice new interview suits and with my newly honed interview skills along with an external candidate was one of two finalists for the role.

Unfortunately, they offered the role to the other candidate. The day I found out I didn’t get the job I got a voicemail from a recruiter for job that was great fit for me. Within two months, I’d gotten two job offers and was actively interviewing for a third job. The job I ended up taking was a much better opportunity for me and resulted in a big promotion and raise. I learned from that experience that sometimes great things can come from big disappointments if you keep striving towards your goal.

What advice would you give to other CEOs and business leaders to help their employees to thrive and avoid burnout?

Stay connected to what brings you joy and schedule time to do those things so you can recharge your batteries. It can be so easy to focus single-mindedly on getting results in your job or business that you lose track of the fact that your energy is finite. It’s very important to move at a pace that is sustainable and to recognize your own needs as a human being. Balance is key to long-term success.

How do you define “Leadership”? Can you explain what you mean or give an example?

You can only be a leader if people are willing to follow you. In order to be an authentic leader you need to engender trust in your followers. That requires that you paint a clear picture of where you will be going, provide inspiration for what the followers will get from coming along on the journey, and provide enough space for people to bring their best to the cause.

Respect is such an important part of being a good leader. When leaders use micromanagement or coercion to get results, they are limiting the impact that they have as leaders. Good leaders create an environment where people can and want to bring their best to support the cause. It requires mutual trust and respect. As a leader it may mean being willing to say that you don’t have all the answers.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

As a coach, I spend many hours each day speaking with my clients about high-stakes situations that they are dealing with. It’s very important for me to remain present and be an active listener in our conversations. In order to do this, I’ll spend a few minutes between sessions clearing my mind and doing some deep breathing exercises so I can be ready to meet each client with positive energy and presence.

When I was a marketing leader at the bank and had to go into a high-stakes presentation or discussion where I needed to get agreement from an executive, I would spend time beforehand visualizing the presentation or meeting going well. In my mind I would play out the event and observe myself being successful. I found that that got me into a state of flow so that when I went into the situation in real life, I felt like I had easy access to the knowledge and capabilities to respond to whatever came up. It worked like a charm. Even when I was thrown a curveball, I didn’t get nervous. I was able to respond with grace.

Ok, let’s jump to the core of our interview. Can you briefly tell our readers about your experience with managing a team and giving feedback?

For 15 years I led teams ranging from 2–30 team members. The employees on my teams had a lot of interactions directly with leaders within the business all the way up to the CEO and if my team members did not meet expectations the business leaders would not hesitate to provide feedback to me. It was in my best interest and those of my team members to provide constructive feedback to the team to ensure that they were set up for success.

As a leader I believe in having consistent processes and providing very clear guidelines to my team members while also allowing them latitude within the parameters of my expectations. I did this by having regular one-on-one meetings with my direct reports that provided a forum for two-way discussion about my expectations and challenges they were facing. I also made it clear that my door was always open if they needed my support.

This might seem intuitive but it will be constructive to spell it out. Can you share with us a few reasons why giving honest and direct feedback is essential to being an effective leader?

A leader’s success is predicated on the success of the people on her team. As one of my mentors used to say, “Your team members are either going to be part of your success or part of your failure. You decide which.”

A leader’s role is to set the agenda for what the team will work on and keep the team moving with pace toward that goal. If there is disagreement or misunderstanding between the expectations of the leader and the activities of the team members, the goal will not be achieved as efficiently as it would be otherwise. Feedback is what keeps the activities and the expectations aligned.

One of the trickiest parts of managing a team is giving honest feedback, in a way that doesn’t come across as too harsh. Can you please share with us five suggestions about how to best give constructive criticism to a remote employee? Kindly share a story or example for each.

  1. It’s important to be direct. Sometimes when we try to soften the feedback, the message gets lost. I like to use the approach of “I’ve observed when you do x, that y happens. I think that we can get a better outcome if you do z. What are your thoughts on this approach?” I once had an event planner on my team who was overly responsive to requests from the business and would sometimes start planning events before we had approval on the budget. After taking more than one call from the head of the business who was not happy about not being consulted on events that his underlings had requested, I called the event planner and said, “When you move ahead with events before we’ve gotten express approval from the president of the division, he gets upset and calls me to give me an earful. Going forward, when you get a request from someone in the business, I would like you to let them know that you cannot move ahead with planning an event until the president has signed off. What, if any, issues do you anticipate if you were to use this approach?” She stated that she was concerned that she’d be perceived as unresponsive to the business if she didn’t get started right away on the requests. I reassured her that I would back her up and that this approach actually protected her partners in the business from spending money that had not been approved. It took a few reminders but she eventually got on board and changed her approach which was beneficial for everyone involved.
  2. As much as possible, give feedback in person or by phone. It’s way too easy to have misunderstandings when trying to convey feedback by email. Having a conversation will allow the employee to ask clarifying questions and for you to speak in a positive tone. It’s understandable that if the message is a difficult one to deliver that you might be tempted to send it by email, but this would be a big mistake. There’s too much risk that they message will either be misunderstood or missed altogether. Having the respect to speak directly to the employee and answer any questions will build trust which will make working together easier going forward.
  3. Approach giving feedback from a position of wanting the other person to benefit. Do not give feedback if you are feeling angry or irritated. Though it can be natural to feel frustrated if you’ve provided the same feedback more than once or if the person’s action put you in a bad position. Nevertheless, make sure you are able to approach giving feedback with a belief that this person had the best of intentions when they took the action. Approaching giving feedback when you are feeling judgmental or with pre-conceived notions about the person’s intention will only result in hard feelings and the person not receiving the feedback in a positive way.
  4. When giving feedback, provide specific examples and provide the feedback as close to real-time as possible. For example, if you notice someone on your team interrupting a co-worker or monopolizing the conversation in a meeting, you may want to intervene in the meeting and say something like, “John, thanks for your input, now let’s give Sally a moment to share her perspective.” Then after the meeting, you may want to pull John aside and share with him your observations about what went on in the meeting. This approach is much more effective than saying something like, “John, I notice that you interrupt your co-workers frequently in meetings.” Feedback that is too vague and detached from an actual instance of the behavior may leave him feeling criticized without an opportunity to understand how he could improve.
  5. Catch your employees doing well and capitalize on it. When an employee demonstrates behavior that you’d like to see repeated, be sure to recognize and praise the employee for it. People tend to repeat behavior that they are rewarded for. For example, in the case of a bright employee who you’d like to see speak up more in meetings, rather than saying, “Sarah, you really should speak up more in meetings,” you may say something like, “Sarah, that suggestion you made in the staff meeting today was really innovative. It sparked a great discussion. I hope that you’ll continue to share your ideas with the team. You’ve got a unique perspective that we all benefit from hearing.”

Can you address how to give constructive feedback over email? If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. How do you prevent the email from sounding too critical or harsh?

If the feedback is positive, you can give it over email. However, I would avoid giving corrective feedback over email. It’s way too easy for it to be misconstrued and to hurt the relationship. An alternative is either to pick up the phone and provide feedback voice to voice, or to send an email and say something like, “In our next update meeting, I’d like to discuss how we can better address the x situation.” This way you’ve given them a heads up that you’d like to discuss the situation, but without going into detail over email. Sometimes people will get a little nervous when you raise an issue like this and it may be reassuring to say something like, “Nothing negative… let’s just add it to the agenda for our next update.”

In your experience, is there a best time to give feedback or critique? Should it be immediately after an incident? Should it be at a different time? Should it be at set intervals? Can you explain what you mean?

I believe that it’s best to give feedback as close to the incident as possible with one important caveat… If you or the other person are feeling emotional about the situation, you should hold off on providing feedback until both of you have had time to regain equilibrium before providing feedback. If you provide feedback “in the heat of the moment” there’s a good likelihood that either one or both of you will get caught up in the emotion which will make it difficult for the conversation to be productive or for the feedback to be received in the way it was intended.

I believe that it’s well worth the investment of time to have regular one-on-one update meetings scheduled with all direct reports at minimum on a monthly basis and potentially even weekly. This regular standing time provides a forum for sharing insights, providing feedback and for both of you to ask questions and align performance and expectations.

How would you define what it is to “be a great boss”? Can you share a story?

To me being a great boss means helping staff members to perform to their highest potential within the parameters of the organization’s objectives. I’ve always been interested in understanding the larger ambitions of team members so that I could keep an eye out for opportunities for them to fulfill those ambitions.

An example from very early in my career was when I was interviewing to fill a print production coordinator role at a small publishing firm. Tracy, a very bright recent college graduate with a degree in graphic design interviewed for the role. The job had very little requirement for graphic design but I explained to her that learning about print production would be complementary to her graphic design skills and better prepare her for future career opportunities. She ended up accepting the job offer and within a year I left to go to another firm. Within a few months of me starting my new job, there was an opening for a graphic designer and I reached out to Tracy about the role. She ended up interviewing and being hired into this job.

This story illustrates what it means to be a “great boss” — it’s about putting things in perspective for the employees who report to you, in looking out for their best interest and advocating for them when opportunities present themselves. I’ve found that when you do these things for employees that as a boss you’re rewarded with loyalty and people who are willing to bring their best every day. That’s what I call a “win-win.”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

My mission as a professional is to help people to recognize and value their own greatness. Too often high-achieving people are very focused on external validation and it begins at a very young age with questions like “Are my parents happy with me?” “What does teacher think about my school work?” “Does my boss think I’m doing a good job?”

I’ve seen many very bright people worry excessively about what other people think of them and it can really drain the energy that could be redirected towards accomplishing things that are important to them.

I would like everyone to recognize that they are on earth for a reason and to realize that no one else needs to give their purpose a stamp of approval for it to be valid. When we can each start cultivating belief in ourselves and start trusting ourselves to do what’s right for each of us, the world will be a better place. None of us need anyone else’s validation. We can validate ourselves at any point and we’ll all be happier when we recognize the power that we have.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Two of my favorite quotes are:

“I never lose. I always win or learn.” — Nelson Mandela and “What other people think of you is none of your business.” — unknown

We all have value. We can’t be held back by fear of making mistakes or of other people’s judgments. I believe that each of us has a purpose here on earth and the sooner we embrace it, not only will we be happier, but it will also make the world a better place.

How can our readers further follow your work online?

My book, Winning the Game of Work: Career Happiness and Success on Your Own Terms is available in paperback and e-book formats on Amazon, Apple, Barnes & Noble and wherever books are sold. The audiobook will be out later this year. Your readers can also follow me on LinkedIn and can sign up for my blog at my website: www.terrybmcdougall.com.

Thank you for these great insights! We really appreciate the time you spent with this.


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