SketchDeck CMO David Mack: Giving Feedback; How To Be Honest Without Being Hurtful

Always ask how your team are feeling, get them comfortable being totally honest by making sure they feel safe, and always push people to take breaks and days off. It’s easy to feel busy and pressure people to work more, but if people burnout and quit you’ll lose a lot more productivity than from them taking a few half-days off here and there.

As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing David Mack, CMO of SketchDeck.

a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing David Mack, CMO of SketchDeck.

Cambridge and Oxford educated Computer Scientist-Mathematician, David Mack (former Barclays Capital & Datoral) combines a strong technical background with an eye for design and marketing. He is currently CMO & Head of Content at his startup, SketchDeck.

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?

Originally, I was working in Barclays Investment bank, but the work environment didn’t fit me and I had the hunger to create something of my own. Me and a friend from college started exploring ideas, and over a year iterated and failed on many things, eventually exploring the kernel that would be SketchDeck (A slide building application for the iPad). We got accepted into YC, and then in the first weeks pivoted to almost complete restart. We relaunched our fast slide redesign service, and slowly started to grow a snowball of demand!

What do you think makes your company stand out?

The quality of our work. We’ve spent six years finding a great design team and honing our process, and it’s a real pleasure seeing the beautiful and efficient designs we deliver each day, in a timely manner. Knowing that we’ve helped many companies scale their marketing efforts and reach their goals feels great.

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

Three days after we landed in California and started the Y-Combinator program, jet-lagged and feeling like strangers in a foreign country, Kevin Hale convinced us to shut down our app and start completely fresh. After much consternation, we agreed to his plan and started the seed that would become SketchDeck today.

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?

When we launched, we vastly underpriced our service. Because we were still recently out of college, we had no idea how much businesses pay for things. We charged about $30 for work that businesses would pay $1,300 for–work that we delivered all by ourselves by not sleeping!

The lesson: A quick google of your competition can quickly teach you a lot, and move you forward a few weeks or months!

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

Always ask how your team are feeling, get them comfortable being totally honest by making sure they feel safe, and always push people to take breaks and days off. It’s easy to feel busy and pressure people to work more, but if people burnout and quit you’ll lose a lot more productivity than from them taking a few half-days off here and there.

How do you define leadership? Can you explain what you mean or give an example?

I like to define it as getting people to do what you need them to without resorting to coercion. You align their interests and passions with the teams’ goals, provide a supportive environment and then have a fun time together achieving stuff.

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?

I’m a big fan of walking meditation. Walk in a low-stress environment and let go of the need to think about things. You’ll keep catching yourself lost in thought, but appreciate that you have caught yourself, then let go again and enjoy a short moment of peace.

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?

I’m currently CMO of SketchDeck, and our team is 100% remote. We’ve been running remote since 2015. Currently we’ve 43 designers, plus project managers, staff and freelancers… thus, giving effective feedback is paramount to our business. And doing it remotely is the ultimate test!

We’ve an AI-powered dashboard where clients and designers collaborate. The project managers are always in touch with our clients, and often the iterations require “feedback expertise” since design projects are hugely subjective–if we want the projects to move, the feedback must be as specific as possible.

We provide our crew with training, because giving great feedback is part of our brand, and we also have to help our clients hone their feedback game. Despite honest efforts, most people don’t really know how to give thoughtful feedback. Some clients even told us that they’ve started using our feedback insights with their teams and have had great results.

“I don’t like it”, “This is ugly”, “I hate yellow” are just a few examples of feedback that isn’t helpful. We even wrote a couple of articles to help our clients express their ideas better! It’s not something we take lightly.

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?

It is simple: the better we are at giving constructive feedback, the better our teams will respond.

When you stop to think from their point of view and try your best to help them, the feedback is most likely to land and make a positive impact.

You also need to find a way to be truly honest if you want to steer people in the right direction. It must be kind, compassionate, but also assertive and resolute.

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.

Compassion is a big piece of it for me. You need to start from a place of truly caring about the recipient and their growth–that really helps guide the success of the rest. It can be easy to feel annoyed at someone and then fling feedback out that hurts them.

  • Stay on your side of the fence

If you haven’t heard that before, it’s all about respecting where someone else is coming from and talking about how their actions impact you. No one knows the motivations behind what happens on the other side of the fence–you can only see the result. So, only discuss why something needs to be changed and ideas to fix it.

This avoids hurt feelings on either side when one person attributes a reason behind the action. Attributing motivation can devolve into blaming someone, such as saying, “you’re trying to ruin my presentation/business with this blue layout!” when the real concern is that it won’t look good printed because the company plans on using blue paper.

By staying constructive and assuming the best intentions of the other party, you can get a high-quality product without a lot of anxiety and stress.

  • Show and tell your ideas

Offer comparisons. Like: “I want a more modern feel, like this other piece” instead of “this looks old”. Take Skype or McMillan Cancer Support brand guidelines:

Logo Demo
Logo Evolution
  • Use the right medium

Some people respond better to different channels. Of course, we can’t have a specific channel for each person, but sometimes it’s the details. Like instead of starting a video conference, a fast call is enough. Some like better to get feedback on their email, others on Slack.

  • Consider word choice

This is very important–not only to avoid being harsh, but also to be clear! And when you work with people who have English as a second language, it is even more important to carefully choose your words.

“Silver bullet” and “hit it out of the park” aren’t universal metaphors, and they rarely “hit a home run” with English as a second language (ESL) people. There’s almost always a simpler way to say what you mean. Try these quick tips to simplify your word choice for better feedback:

  • Instead of “utilize”, say “use”
  • Instead of “exhibit”, say “show”
  • Instead of “advantageous”, say “helpful”
  • Instead of “disseminate”, say “spread”
  • Explain your decisions

When giving feedback, always explain your decisions. Instead of saying “I don’t like this, try again”, approach it on a more constructive way. For example: “This font is not working because it’s too heavy and condensed to use at such a small size. For smaller text sizes, always pick a font with good readability, like Helvetica. Leave fonts with more personality like heavy condensed ones for titles, where they can be appreciated better”.

Provide examples and ideas on how to solve things that are not working. Leave it open for them to propose something else, but it’s helpful if you can describe how you think it could be solved.

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?

The best way is to remember the ABC rule — Always Be Compassionate. If someone asks you: “hey, I’ve done what you asked. Is it good?” instead of saying “no, that’s bad, do it again” you should say: “Hey, thank you for delivering it! To be honest, there is a lot of room for improvement. But I think it has potential–why don’t we try doing it this way instead?”

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?

In my opinion, depends on who’s giving feedback. If you can manage your emotions and do it politely even if you’re steaming, do it right away so you don’t need to waste energy thinking about the problem. But, if you know yourself and you tend to explode, give yourself some time to settle down.

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

Being a great boss is putting your team members first, and truly being compassionate to their needs. I’ve been fortunate to have a lot of good bosses. Last year I had a really crushing breakup, and it really impacted my productivity. My boss regaled me with his stories of heartbreak and never made me feel bad whilst I healed.

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. 🙂

It’s always hard to pick one issue in isolation, but if I had to it’d be global warming–we’re sleepwalking into a scenario that could really hurt a vast number of people around the world, destroying their homes and livelihoods. COVID has shown us that we can stop flying around the world and still continue our lives, so the movement would be to vastly reduce CO2 emissions from transport by enjoying the places close to home.

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

The boy scout rule: Try to leave things a bit better than how you found them. I try to apply this everywhere: from company folder organization to bringing litter bags on my walks. I like this rule as it’s a simple way to collectively improve the world.

How can our readers further follow your work online?

Our blog at and specifically on this subject, we’ve two articles:

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

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