Penelope Barton of Crimson Education: Giving Feedback; How To Be Honest Without Being Hurtful

As an executive, a mother, and an entrepreneur getting my balance right has been an ongoing evolution. Whilst I fit a lot into my day, I am also selective of where I invest my time and energy, focusing on work that gives me as much as I can give to it. The hours that I spend each day are an investment and a conscious choice for how I am living my best life.


As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing Penelope Barton, Chief People Officer of Crimson Education.

Penelope Barton is Chief People Officer of Crimson Education, an edtech start-up that provides university admissions consulting to families around the world. Since Pene joined as an executive in 2017, it has scaled to now operate in 25 markets with over 320 employees and 2,500 contractors. In addition to being its first appointed CPO, Pene has also worked in the HR team of now multibillion-dollar valuation SaaS company, Xero, for which she supported US, UK, Australia and New Zealand (ANZ) global sales and marketing teams. Pene also worked with SaaS point of sale and retail management software platform, Vend as CPO. Pene is passionate about the future of work, building high growth scalable organisations and the use of AI and Automation to help organisations, their people practices and ultimately their people thrive.


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 have always been an entrepreneur. From selling sherbet to kids in the playground (I am sure teachers loved me!) to launching summer holiday programs as a seven-year-old — if there was a gap in a market I was there. Around the time I was 15, a friend of mine at a movie theatre was late to work and was called into a disciplinary meeting. I went along as her support person. I remember walking into what felt like a cold meeting, where bureaucracy and process reigned and no-one spoke the truth. There was a clear business need for people to be on time to work, but why was it wrapped in this process? Why couldn’t people just be direct? I could see my next opportunity emerging. I was hooked. I set out from there to make it my mission to transform “HR”. I am privileged to have worked in some of the fastest growing tech companies that mirror my vision for growth, transparency and building better workplaces. Along the way the entrepreneur journey has kept calling my name and in my spare time I have also launched and sold food trucks and successful restaurant businesses.

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

I joined Crimson Education back in 2017, when there were around 50–100 people around the world, and the founders at the time were 22-years-old. They had raw intelligence paired with infectious enthusiasm and boundless energy. When you have started a company so young, there is no preconceived notion of how things “have” to be done. There is no impossible — everything is an opportunity, and the same applies to the people — anyone can learn how to do a job, be it a university student or a parent — it has always been a melting pot of potential and possibilities.

A good example of this was my first week. We were 30–40 people crammed in this little office designed for around 20 people and my “easy” task — launch 15 new global markets in the next three months. Fifteen. I have worked in fast growth companies, where we launched a new market, maybe two in a year. This was another level. I nearly spat my coffee out. But you know what, we did it, and those markets have gone from strength to strength over the last two-and-a-half years. Going into that challenge, there was excitement in the air, but never fear. No-one ever said it was impossible.

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

My career has been such an amazing ride, I have been fortunate to work with amazing people, across all industries and across the world in now 25 markets. I have built teams from scratch, integrated them from company acquisitions and facilitated de-mergers. So many stories to tell.

On the topic of feedback though, one moment that comes to mind though, would be the workshops I ran in our global offices on feedback and working style. I recall my first trip to Bangkok, I was expecting quite a lot of cultural differences in the way we would approach the feedback sessions and setting feedback norms. But I found at the core of it, people want the same things, they want to trust their manager, they want feedback that helps them grow. There is something so empowering about having genuine feedback and development conversations and everyone wants it — once you have had it once, you get hooked, and regardless of cultural differences, the core elements remain unchanged. There was also something pretty special about having these sessions translated sentence by sentence — particularly the sessions in Korea, China and Thailand.

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?

About 10 years ago, I was working in a large corporation. We were growing fast and I was working closely with the Leadership Team on de-merging two companies. It was a high stakes project, one that you only get to do once in a lifetime. I was early-ish in my HR career, and wanted to make a good impression. When I was onboarded, my name was spelt wrong as ‘Penny’, instead of ‘Pene’. I didn’t want to correct anyone, didn’t want to rock the boat. About eight months later, I was at a relay event for charity with the CEO. It’s 4am in the morning, everyone is slightly delirious given the time and somehow in the conversation It came up that my name was actually spelt wrong. He was outraged (and bemused that I would let this go on for so long) — I remember him telling me to either update my email today, or in our next company call he was going to tell the whole company how to spell my name correctly so that from that moment on, no-one would get it wrong. I quickly had it updated, and I remember at the time thinking, ‘this would have been so much simpler if I had just told the on-boarding staff member how to spell my name’. Those who know me now would probably be surprised to hear that — I have definitely shifted towards communicating with a very transparent and direct style.

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

Three things you can focus on in your team to avoid burnout and thrive at work — Clarity, Accountability and Purpose.

The most important thing you can do first as a leader out of these three is create clarity for your team. When it’s your own business, you might see a healthy work-life blend as being always ‘on’, messaging in the middle of the night, working on multiple different projects and sending tasks to everyone because you had a great idea and it needs to be delivered today. It can be hard to keep up with that intensity and not get burnt out — it’s an inevitable cognitive overload. I see this happen a lot when individuals are new to work, or in a new job — people want to emulate the behaviours of the leaders and the most successful people in the company. It doesn’t matter if your company values wellbeing and has an unlimited annual leave policy to reduce burnout, your actions as a leader will dictate the behaviour.

Always ask yourself “How am I creating clarity for others around me?”

From there, be explicit on outcomes for individuals in their role — what they are accountable for, and role model behaviours you expect of others. Even if that means you keep a pen and paper next to your bed so you jot down all your thoughts rather than sending them off to people in the middle of the night.

So to recap, you create clarity, which allows you to give autonomy to your team — that in turn leads to greater motivation — and then you focus on building purpose and pulling your people towards that vision.

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

Leadership to me is creating the environment for others to succeed. It’s not selfish at all, or about your own success or status.

The best leaders I have worked with are in it for the team and the business. They have a clear vision aligned to the business, they set goals for the team that leverage the strengths of the team, they connect individuals to support their projects and their growth, they give feedback regularly and they move roadblocks before people even know they existed. I always think leadership is quite analogous to the sport, curling. You have one person that slides the stone out on the ice, and supporting that person you have your sweepers that are out just ahead, working hard, brushing the ice in a way that guides the stone to perfectly slide to its final landing place.

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 fast growing team we encounter this a lot, and I run sessions with our global team on how to perform under pressure, which is a combination of proactive practices, but also what you do when you get into a heightened state or before you have a big meeting/decision.

Proactively, some practices I follow — at the start of each day, setting an intention “Who is the person I want to be today, what do I want to be known for?” so that I go into the day with intention, and then at the end of each night, I journal three things I am grateful for. I recommend you take this time to do a stocktake and reflect. It’s so easy to get trapped in a blur of day to day and then index on the negatives and stressful situations. This practice will help you reflect and exercise gratitude. Even if I feel tired at the end of the day, I can jot down three bullet points, or three words — it doesn’t have to be a novel, it’s about building the habit everyday so that it alters your mindset.

Before I go into a high stakes meeting, I do two things — first one is a bit odd, but I do a skip/hop/shake on my way to the meeting, just to loosen up a bit, then second thing is I try to oxygenate. If I can take one minute, then I focus it on mindfulness, or if I am running late into a meeting, then I take a three second pause before I enter into a room and take a couple of deep breaths. Sometimes it can look a bit awkward that I am hovering outside a meeting room door (particularly If I just skipped up to the door) standing quietly — but three seconds, centre yourself, take some deep breaths. It makes a world of difference.

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?

My role as Chief People Officer is not your typical “HR” role. I spend 50–60% of my time in 1:1 leadership coaching. That could be new leaders, seasoned executives or high potential individuals looking to move into a leadership role. In every organisation I have worked in regardless of industry, one of the fundamental skills we focus on building first is feedback. Its core to every aspect of managing and leading a team. Working with leaders who have teams of 200+ to leaders of teams as small as 2, most situations that you encounter will have some aspect of feedback — either to reinforce the behaviour you want to see, or to enable courageous conversations.

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?

Regardless of size, to work effectively as a team you need to have psychological safety. It will set you up for high performance, for creativity, for an environment in which people can do their best work (thanks to Google for the depth of research in this area). One of the ways to establish this is through building human connection through honesty and transparency. Giving honest feedback is a great way to demonstrate to your team you are invested in their development and are there to support them. I would also add — feedback is two way, so don’t just give feedback to individuals on your team. Ask for it as well.

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. Don’t assume how you would like to receive feedback is how another person would. Talk to your team about how they like to receive feedback, i.e. is it via email, Is it a phone call, or a video. Some people have had horrible experiences from feedback in the past so it can be quite a traumatic experience. Work to set some norms with your team first. I have people in my team who prefer I email them key points, then they digest and we discuss later, and others who like direct feedback in the moment.
  2. Consider the environment — too often I see managers give feedback in front of a whole team, in a meeting or in an open plan office (when that was the norm). Consider not just the feedback itself but how it’s being delivered. In our current WFH model, it’s harder to control this environment — you could be giving feedback and their child is sitting right next to them, or their family is in the background, leading to a very demoralising experience. Assuming you have set some norms with your team member on how they like to receive feedback this should be a bit easier. But if in doubt, make sure you do a video call with cameras on, and check with the person if now is a good time.
  3. Practice the same model for positive and negative feedback. Constructive feedback is specific, timely, accurate and has clear action steps. Stop thinking about constructive feedback as only negative. It is just as important that someone knows what they did that was effective, what specifically about it hit the mark, and how they can replicate it again in the future. Avoid “good job, and great work” as defaults for positive feedback.
  4. Before giving feedback, check that the intention of giving the feedback is to help the other person. Feedback that makes you feel good, or because someone said “tell this person to improve their presentation skills” won’t land.
  5. Build feedback habits in your team. Hearing feedback every once in a while makes it a bigger deal than it needs to be. Consider ways you are building feedback habits in your team. One practice I use in my team is every Friday we go around in our team stand up and tell each other one thing you admired the other person did that week and one “EBIF” which stands for “even better if”. Doing this on a regular basis within a healthy team environment creates more safety within the team to give and receive feedback.

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?

Unless this is set up in advance as the way someone prefers feedback I usually counsel against this. You can’t control the environment at the other end of an email, the headspace they will be in, what email they might have read before yours. Add in different cultures and words can be misconstrued.

If it’s your only option though, I would ask:

1. Is this your usual normal channel of communication? If you use microsoft teams, whatsapp, slack, is it better sent via that platform directly to the person? Shifting to email can make things much more formal than needed depending on your workplace culture.

2. Keep it brief. Outline your intention for sending the feedback, the observation, the impact and next steps. Don’t over-explain, add in superlative words, or terms such as “I think” which is obvious as you are the one writing the email. It can seem judgemental. Another tip is don’t compare someone’s behaviour to one of their colleagues i.e. “Christine was great in that meeting”. Focus on the specific observations you had about that person, and the impact you noticed. The clearer and less open to interpretation the better and more likely it is to be received well.

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?

Where possible, immediately after something has happened — good or bad. The more timely the feedback the less open to interpretation it is — both sides have a clear recollection of events. I try to avoid repetition as it can quickly become “oh here comes Tuesday 1pm, my boss is going to confront me with everything I have done wrong”. That being said, I have some people on my team who prefer we cover it as part of a broader coaching and development conversation in our 1:1s, so in those cases I wait until then.

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

Around 10 years ago, I was fortunate to work with an amazing leader. Sara. She gave me a lot of trust and autonomy, but the standards she set for me were unwavering. You would never say the words “I will try” to her, as she would immediately quote Yoda “there is no try” back. It wasn’t done in a way that was critical, she just knew that you were pushing something down the line. She really brought out the best in me. I knew the work I took to her needed to be high quality, yet at the same time, If I made a mistake that was never an issue — she was a safety net at the same time she was pushing you up, as she was there to develop you — not for her own gain. She was also eternally optimistic, with a clear vision and purpose. I think back now on how easy she made it look and the work I have done myself and with others to replicate some of these traits. It must have been no easy feat.

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. 🙂

A movement to share more of your knowledge. Mentor, talk, present — don’t hoard your knowledge for fear it makes you more “powerful”. The more you share, people can build on your ideas, bring you a different viewpoint. It’s how you grow. I really resonate with Crimson’s goals around connecting mentors with students around the world for this very reason. I would love to see more connections for growth happen organically around the world.

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

“When you lose track of time, you are either living your best life or wasting it.” James Clear

I saw this quote recently in a weekly newsletter, and it immediately resonated with me as something that’s always in the back of my mind as I make decisions. It’s so easy to get swept up in work, in the busy-ness, in life. As an executive, a mother, and an entrepreneur getting my balance right has been an ongoing evolution. Whilst I fit a lot into my day, I am also selective of where I invest my time and energy, focusing on work that gives me as much as I can give to it. The hours that I spend each day are an investment and a conscious choice for how I am living my best life.

How can our readers further follow your work online?

Linkedin, or keep an eye on the Crimson Education team.