Stacy Richards of OysterReef Coaching: “Seek out feedback for yourself regularly”

Seek out feedback for yourself regularly. When you are the recipient of feedback you personally understand the impact it can have, both good and bad. You will be better able to take your recipient’s feelings into consideration. Get comfortable with asking this question on a regular basis: “what is one thing you see me doing […]

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Seek out feedback for yourself regularly. When you are the recipient of feedback you personally understand the impact it can have, both good and bad. You will be better able to take your recipient’s feelings into consideration. Get comfortable with asking this question on a regular basis: “what is one thing you see me doing or not doing that gets in my own way?” Also make sure you ask a variety of people — your boss, your employees, your customers, and even the people with whom you have the most challenging relationships. They are the ones who are likely to be most honest with you!


As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing Stacy Richards, Founder and Head Coach at OysterReef Coaching, LLC.

Stacy is an executive coach passionate about coaching young people, with twenty-six years of experience as a lawyer and corporate sales leader. She is a frequent presenter and facilitator, from audiences of hundreds, groups of executives, lawyers + federal judges to women’s executive groups and college student organizations. Through her PRACTICETM Method, Stacy coaches and inspires driven young professionals to exude confidence, lead with empathy, seize opportunities and succeed wildly in a fulfilling career.


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

I grew up as the oldest of four kids, the “student” in the family, and declared that I wanted to be a lawyer at the age of 7. During my senior year in college, I panicked a little because I had no idea why I wanted to be a lawyer, other than I thought I would make a lot of money! So I decided to work as a paralegal first. I did that for two years, still went to law school, practiced as a litigator for 2.5 years, and then left the practice of law. I was lucky to land a role at a global company that provides information to the legal profession and developed a very fulfilling career there in sales and sales leadership.

The moments I enjoyed the most in any of my roles as my career developed involved teaching or coaching, often young people who joined my team. In fact, even when I was practicing law, I moonlighted as an SAT/LSAT/bar review tutor. Continuous learning has always been a strong value for me, and in 2018 I enrolled in an online program called the altMBA (developed by Seth Godin). The program made a huge impact on me and transformed what I wanted to do with the rest of my career. I became a coach in the program, which I do to this day because I love it so much. Then when the pandemic hit in early 2020 and all the travel I had been doing in my role as a sales leader came to a screeching halt, I used the extra time to develop my own coaching business.

My daughter graduated from college this year, and my son is a sophomore in college. I realized how much impact I could make by focusing my coaching practice on young professionals, as they graduate from college and enter a rapidly changing workforce. Interpersonal skills, what we used to call “soft skills,” will be more critical than ever as we re-think the workplace, and these are skills that we just don’t focus on in traditional education. That’s where I decided to focus my coaching practice.

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

Over 26 years, there have been a lot of interesting stories! Although, one story comes to mind as it relates to the topic of feedback. In my first corporate job, I was responsible for training law school students who were serving as federal court clerks in our online research system. It was daunting, because these students were the best and the brightest, and I was only a few years older than them. After I finished training a large class of law clerks, one of them approached me and spent the next twenty minutes berating me for all the parts of my training she thought were ineffective. The whole tirade happened in front of my “client,” the law librarian, who stood by and said nothing in my defense. That was one intense way to learn about receiving feedback! It took me a few days to recover from that one, but I’m proud to say I went on to effectively teach many more classes over the years.

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?

I’m glad I can laugh about this one now, because at the time it was very stressful! In my first corporate role, I had a conflict with one of my colleagues. We were both relatively new and in the same role. At the time I would have told you she was very competitive, but I’m sure we both were and that contributed to the conflict. Things escalated when I felt she was trying to undermine me and make me look bad. I obsessed about the situation, to the point where I printed copies of emails to share with friends during a dinner out, as evidence for my side of the story! I hijacked that whole dinner, and we laughed about it for years after.

The lesson I learned is that over the course of a career you are going to have lots of differences of opinion or even full-blown conflicts with others. Never say out loud, or type, responses in the heat of the moment. The only thing that matters in those situations is to stay true to yourself and your values and defend yourself if necessary, with full respect for others.

I wish I had heard the Michelle Obama quote “when they go low, we go high” at the time, as it would have been helpful advice!

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

We need to shed workplace traditions that are no longer serving us — things that came out of the assembly line mentality of the Industrial Revolution. Now we’re in the thick of the Information Revolution, and the pandemic has rapidly accelerated the demand for change. The best CEOs and business leaders over the coming years will be those who place the health and well-being of their employees at the top of their priority list in addition to profitability.

We know that more employees are feeling burnt-out than ever and are reevaluating their careers. Employers will continue to lose quality people as part of the “Great Resignation” if they don’t quickly take action to ensure a thriving workforce. Every employer should be considering remote and/or hybrid work, flexible schedules, etc., but they should also take a close look at the leadership strengths of their managers. Are they: checking in regularly with their team members, asking questions about how they are doing personally and professionally, whether they are feeling challenged and fulfilled in their roles, what their advancement goals are, how they would like to be growing and developing and how they can, as their manager, can help? Basically, strong interpersonal skills and emotional intelligence should be a requirement for every manager, so that each employee feels a sense of safety and belonging. If your employees don’t feel that psychological security, it’s impossible to thrive.

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

Leadership is a process that takes time. Great leaders provide a solid foundation by demonstrating the ability to care about others more than themselves, put their team members’ needs first, make them feel safe, encourage them to be their best selves, provide a positive environment for them to thrive and then ask them to follow and contribute to a greater cause. When you wholeheartedly trust someone who says, “come on, let’s go do this great thing together,” even when you know you will be facing huge obstacles, you are working with a great leader.

This probably seems like a cheesy example, but Princess Diana comes to mind. She never sought to be a leader, but she visibly lived her life with care and compassion for others as her driving force. Despite the drama surrounding her life, people trusted her because she was genuine, always prioritized the needs of others and made them feel safe. When she realized the power and influence that she had established globally, she relentlessly used it for good — particularly for AIDS patients at a time when they were shunned. She will forever be remembered for her compassion and defiance of protocol when she held the hands of hospital patients without using gloves. She was instrumental in changing how the world treated individuals with AIDS. I can’t think of a more powerful way to lead.

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?

To this day, I still get anxious before every important presentation or high-stakes meeting. Luckily, I had a beloved professor in law school who told us the day you don’t get nervous before a legal argument is the day you should really start to worry. He was absolutely right! The reaction in your body to anxiety is the same as excitement — it’s an adrenaline rush. So, I tell myself it’s important to me, and I’m excited about it, so of course I feel that way. I also know that rush helps me to perform at my best.

I try not to let myself get caught up in traditional advice like “make sure you get a good night’s sleep,” because my nerves usually disrupt my sleep before an important day. The things that I’ve accomplished that I’m most proud of almost all came with poor sleep the night before, so it must be working for me!

And finally, I remember to put things in perspective and just breathe.

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?

Feedback is widely considered to be one of the most difficult conversations to have, for both the giver and the receiver. I have learned so much about myself and my effectiveness as a leader by managing teams and giving feedback. I’ve made a lot of mistakes, and I have realized over time that my humility and willingness to admit mistakes or apologize are much more valuable as an effective leader than being right or perfect. What I describe to my coaching clients as “confident humility” is critical when managing a team and giving feedback. A good leader will be prepared and confident in their skills, but also willing to learn new things and admit to mistakes. In the case of giving feedback, you want to prepare thoroughly for the conversation and be confident in the message you are delivering, but also willing to hear the recipient’s viewpoint and change your assessment if warranted. By leading with confident humility, you are also modeling valuable skills for future leaders on your team.

Giving feedback is one of the hardest parts of being a manager at any point, but especially when you’re new to the role. When you reflect on how much formal feedback has impacted you own career, you realize how important those conversations are and therefore how thoughtfully you should approach them.

I remember a time when I had to make a hard hiring decision. I had two great candidates on my team who both wanted to be promoted. When I delivered the news to the candidate who I had not selected, and gave him my reasons why, it didn’t go well. As the highest performer on the team, he thought he should have gotten the job. I knew it was important that I give that person thorough feedback, a complete picture of why they weren’t chosen so they would be able to adjust and be better prepared for future advancement opportunities. I spent quite a bit of time preparing for that conversation and learned a lot about the importance of actively listening while giving feedback, especially when the conversation doesn’t go as expected, and giving the other person ample time to ask questions and say everything they wanted to say.

I still get nervous about feedback conversations because I consider them so important. I try to focus on striking the right balance between pointing out ways a person can improve with all the things they do well. It’s also very important to convey confidence that the team member will be able to improve with the feedback, and a willingness to help and support them in the process.

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?

You can’t be an effective leader without having the ability to give honest and direct feedback. As I mentioned, it can often be the hardest task as a manager, and for that reason many managers avoid it. They rely on quarterly or yearly written evaluations instead of giving helpful feedback in the moment (or shortly thereafter to respect privacy), when the recipient is best able to understand and receive it. As a young manager there were several times when I held back on giving feedback that could have been helpful because I was unsure of how to phrase it correctly or too afraid that the recipient would be unhappy. The bottom line there is, I wasn’t doing the work required of a good leader.

When you are learning a new skill or improving on the way you do something, the best way is to practice yourself. In a work environment, when a good leader sees an opportunity to help you improve, if they don’t point it out to you, how else will you recognize the opportunity, practice, and get better? That’s why the role of the effective leader in taking the initiative and giving the feedback is so critical — you are providing the recipient with a solid foundation for improvement.

Some leaders may give feedback regularly but do so in a way that’s unclear or incomplete. That’s not effective for the recipient. The feedback must be honest, delivered with care and consideration, and clear and direct rather than vague or too general. So, there’s a lot of thought that should go into giving effective feedback as a leader.

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.

Based on my experiences as a leader, with quite a bit of trial and error, here are my five top suggestions for giving constructive feedback without being too harsh, whether the employee is in the office or remote.

First, seek out feedback for yourself regularly. When you are the recipient of feedback you personally understand the impact it can have, both good and bad. You will be better able to take your recipient’s feelings into consideration. Get comfortable with asking this question on a regular basis: “what is one thing you see me doing or not doing that gets in my own way?” Also make sure you ask a variety of people — your boss, your employees, your customers, and even the people with whom you have the most challenging relationships. They are the ones who are likely to be most honest with you!

Second, practice empathy. I say “practice” because none of us, as human beings, are ever perfect at empathy. When we’re empathetic we are putting ourselves in our feedback recipient’s shoes — their feelings, opinions, experience, etc. When you prepare for a feedback conversation, think about that person’s past experiences, personality, position on the team — anything that you know about them that will help you better understand why they might behave the way they do and how they might receive the feedback. For example, if you have an employee who has been seeking a promotion for a while and hasn’t received one, how might they be feeling? What might motivate them to hear the feedback with an open mind and act upon it? Your preparation for a feedback conversation, including practicing empathy, will go a long way in making a positive impact.

Speaking of impact, my third suggestion would be to consider your intent versus the impact of your words. The best example of this I can think of is a conversation I had frequently with my kids when they were younger. It went something like this:

Son: “Yeah, Mom, I’m going to do it. You’ve told me like a thousand times.”

Mom: “Please don’t be rude.”

Son: “I wasn’t being rude . . .”

Mom: “That may not have been your intent, but that’s how it felt.”

You get the gist. Once again, preparing for the feedback conversation will help to avoid this pitfall. Think through exactly how you will convey the feedback, and perhaps even run it by an objective third party first. Make sure your words or tone of voice aren’t clouding effective delivery of important feedback.

Suggestion number four is to balance coaching with appreciation. There are three types of feedback: evaluation, coaching and appreciation. Evaluation is something the recipient can’t change, such as “you received a 3 rating on your performance review.” Coaching gives the recipient something to work on, and optimally gives them suggestions on how to improve. Appreciation is positive feedback, the kind we all love to receive. Your feedback will be much more effective and likely to be acted upon if the recipient feels a balanced approach, including both positive things and the opportunities for improvement.

Finally, and perhaps most importantly for an effective feedback conversation, make sure your internal voice doesn’t interrupt the conversation. We all know the voice — it chatters constantly when we’re alone, with a loved one or even in a large group. Some people describe it as the narrator of their life. So, during a feedback conversation, it will sound like “wow, I’m trying to give her helpful feedback and she is getting defensive. And by the way, what she just said about me isn’t true.” It’s challenging but do your best to quiet that voice so that you can focus completely and generously on the individual receiving the feedback. When you’re not distracted by your internal voice, you are better able to hear what they’re saying but also read their non-verbal cues, then course correct if needed and get the conversation back on track.

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?

This is such an important question. Especially in today’s remote or hybrid work environments, email is sometimes the only way we can give timely and effective feedback. I have this conversation often with my coaching clients, who are learning the pitfalls of misinterpretations through written communications at work. Not only can you not read facial expressions or body language from the message deliverer over email, but they have the luxury of “speaking” without you standing right in front of them. The result is that people can be a lot bolder or brasher with their email language.

Effective leaders obviously avoid that temptation. When you are giving feedback, or delivering any message at all by email, it’s important not to write quickly, especially when your emotions are running high, and press “Send.” Try typing the message and then saving it in draft in those situations. Come back to later when you are calmer and more objective. Then, read the draft with empathy in mind. How might this person receive it? Have I been mindful of any special circumstances (like a personal situation or recent setback)?

If you have received feedback in the past yourself that your emails can come across as critical or harsh, you should be especially mindful when giving feedback to others by email. Think about someone you love receiving that same feedback — would you feel like they were treated fairly and communicated to with consideration? Perhaps have someone else read through it for an objective opinion before sending. A fellow manager can be a great resource for proofreading purposes.

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?

There is not a single right answer to this question. Sometimes, it will be important to give feedback immediately. For example, let’s say you are coaching a new team member who is making outbound sales calls. In one call, they say something to a prospect that is outside your company’s protocol. It’s important to give them immediate feedback on a better way to state, before they make their next call, so they don’t make the same mistake again.

At other times, your emotional intelligence may tell you that it’s important to provide feedback, but right after the incident is not the best time because of the recipient’s emotional state. Let’s say you have attended an important client presentation with an employee, and they make a critical mistake that could cost you the business. With something that crucial, they are likely to know they’ve made the mistake and feel pretty devastated about it. In that case, the most effective approach once you leave the meeting would be to say, “OK, we both know that didn’t go as planned. It’s been a long day, so let’s take a break and talk through it tomorrow morning.”

The biggest mistake managers make with feedback and timing, as I alluded to earlier, is to hide behind the quarterly or annual reviews to provide feedback for employees. Those reviews should be a summary of feedback that you’ve provided in the moment or shortly after with every situation that arises. It should never be the first time that an employee is hearing any type of feedback.

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

While I don’t think there’s any one definition of a great boss that applies for every employee and in every industry or function, I think there are some universal adjectives or phrases that people use when they describe a great boss they’ve had: calm under pressure, resilient, confident, humble, kind, empathetic, fair, equitable, optimistic, good listener, hard-working, good communicator, removes obstacles, willing to admit mistakes.

Wow, even as I type it, that list seems very daunting. The reality is that no one human can be all of those things all day every day. I think the key is that when leading other humans, a great boss typically knows when each of these qualities is needed and can deploy it at the right time. I say typically because, the best boss in the world will make mistakes on occasion because sometimes they need to take calculated risks. When they make a mistake, they admit it openly and widely, and set the example of how to move on and do better the next time.

I’ve been lucky enough to have had many great leaders to learn from during my career. One example that I’ve been thinking of lately is the leader I worked for in my favorite corporate role. It was a big jump for me, leading a much bigger team and responsible for creating an additional division. He put me through a long and arduous interview process, but once I stepped into the role, he gave me a lot of independence to create the new team as I envisioned. The most important thing he did for me was to empower me. He asked good questions with every proposal I made, pushed me to think of things differently, and in the end allowed me to make critical final decisions myself. He gave me tremendous confidence in my leadership and strategic abilities and allowed me to push myself further than I ever thought I’d go as a leader. He provided a wonderful example that influenced my leadership style after that, and how I try to coach and empower my clients now. Hopefully I have “paid it forward,” because great leaders leave impressions that reverberate with subsequent leaders long after their own retirement.

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. 🙂

For those who have worked with me or talked with me about my coaching philosophy over the last four years, this is an easy one. EMPATHY. If I had to boil down the legacy I want to leave, it is the appreciation of how important our practice of empathy for one another is to the healthy future of our workplaces and our planet. Yes, if I could trigger a worldwide EMPATHY PROJECT, that would be the ultimate dream.

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

I am a quote Junkie. I have them on bookmarks, on my laptop, on post-its all over my office. So, it’s really hard to pick one and my favorite is sort of like the flavor of the month. Right now, I am centered on a very simple but elegant quote by Robert Ingersoll, “We rise by lifting others.” I am challenging myself to be motivated by it in every interaction I have, most especially with my coaching clients.

When we use our interactions with others to provide the space for them to see their own worth and potential, we are providing a gift to ourselves, to that person and to every person that they then impact in a positive way with their gifts. It’s the gift that keeps on giving. I’ve been so lucky to have people in my life who have lifted me up along the way and seen myself and my potential the way they do. I hope to stay hyper-focused on this goal for the rest of my coaching career, and my life for that matter!

How can our readers further follow your work online?

I would love to connect with anyone who is passionate about the art of feedback, empathy, interpersonal skills, and coaching our young professionals to lead better workplaces in the future. You can find me at www.oysterreefcoaching.com and sharing thoughts and questions on leadership regularly on LinkedIn. And hopefully I’ll have the opportunity to share my thoughts on other topics in the future with your readers at Authority Magazine!

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

Thank you for having me! It’s been a true pleasure to think about these questions.

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