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Chris Wilson of Smart Furniture and Office Designs: “If everything goes according to plan, we didn’t try hard enough”

“If everything goes according to plan, we didn’t try hard enough.”Have a plan, execute it well, but don’t be afraid to stretch. Your goals should be ambitious enough that you can’t always hit them. As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure […]

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“If everything goes according to plan, we didn’t try hard enough.”Have a plan, execute it well, but don’t be afraid to stretch. Your goals should be ambitious enough that you can’t always hit them.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Chris Wilson.

He is the CEO of Smart Furniture and Office Designs, online home and office furniture retailers. For years, remote teams have powered the sibling companies as they’ve partnered with businesses across the United States to create workspaces that promote innovation, collaboration, and productivity. In the age of COVID-19, they are leveraging their experience to help business leaders equip their dispersed employees with the same environments they’ve grown accustomed to in office settings.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I serve as the CEO of Smart Furniture and Office Designs, two Chattanooga, Tennessee-based online retailers of home and office furniture. Prior to my current role, I served in marketing and product roles at two startups. (Fun fact: I actually interned at Smart Furniture in college and then spent several years in full-time roles upon graduation. I was excited to rejoin the team as CEO in 2018.)

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

COVID might be it — our business has changed dramatically two or three times this year, undergoing changes that normally would take 12–18 months. We’re a home office retailer, so you can imagine how the pandemic has affected our sales and marketing tactics. I don’t know if there’s ever been such a massive, rapid change in the way people work and the furniture needed to support them before COVID. Being a part of that has been a wild ride the last few months, and we’re excited about what the future holds.

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 once made a pretty big pricing error on a new marketplace. We were adding several hundred items to a new sales channel, and I made a typo where I incorrectly entered a price of 2,799.99 dollars as 279.99 dollars. Of course, someone found this steep, accidental discount and purchased the item before the error was fixed. Fortunately, the customer was understanding and knew the price was wrong, and we did not lose money on it. The lesson learned here is pretty obvious: Details, details, details. Always get the little things right and have good systems of testing/checking.

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

Not everyone shares your inherent passion and motivation for the business, and that’s ok. It’s your job to figure out what does motivate people, what gets them excited to come into work, and ensure that motivation aligns with where you need to go as a business. Accountability and responsibility work well in accomplishing this goal — if you hire the right people and clearly communicate the right goals, they’ll get energy from taking ownership of something they enjoy and have a greater chance at success in their role.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Smart Furniture has almost always had remote teams. Our warehouse, retail store, and HQ office are all at different locations within Chattanooga, and multiple key staff members are remote. We even have a Chicago-based sales team as a result of our recent acquisition of Office Designs. In some respects, completing that acquisition in October of last year — and then immediately kicking into holiday sales madness — was a blessing in disguise. It was a pretty stressful time for us, but it better prepared us for the intensity of COVID and rapid changes we’ve dealt with.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

  1. Communication. Not being in the office together and changing the formats of meetings makes communication both “up” and “down” the chain of command difficult. We’ve been working to ensure people still know what the goals are, and that managers have good visibility into what is getting done.
  2. Culture/connection. You can lose that team atmosphere, people can feel isolated, etc. For us, it’s actually been a good exercise to have everyone remote. Since we always have some remote team members, having this experience has given leadership a first-hand look at what it’s like to spend all your time in a remote work setting.
  3. Meeting creep. People still need time to get work done vs. spending all day on video calls, but with the lack of face-to-face, in-office interaction, they may come up against roadblocks that need to be discussed.
  4. Burnout/stress. Especially with COVID-19, plus the general state of the world, stress levels are by default at a 6 or 7. Add in work stress, and it’s easy for people to spiral. Also, with work-from-home, it’s easy to get sucked in to being “always on” — working longer hours, not taking breaks, etc. And with the work-from-home setup, there’s no opportunity to leave the office and disconnect. Your “relaxation space” is now your office, and people tend to take less vacation when there is nowhere to go.
  5. Training. It’s much easier to train in-person than on screen-shares or calls. As we’ve hired new people over the last couple of months to keep up with the increased volume, we’ve been forced to adapt our training to a remote reality. It’s been a learning experience. Remote training shines a bright light on every aspect of the business that is not well documented.

Based on your experience, what can one do to address or redress each of those challenges?

  1. Communication. We have standardized our team meetings (both full company and specific teams) to have more set formats that will cover important information and encourage managers to present relevant points to the broader team. We also added two midweek team check-ins to make sure everyone understands where the business is, given how quickly things can change.
  2. Culture/connection. Schedule regular team calls (whole team + peer teams) to facilitate interactions. Schedule and plan social hours (coffee breaks, etc.) so that people can still connect and not be limited to transactional work conversations.
  3. Meeting creep. Make sure meetings have an agenda and stick to it to avoid hours and hours of meetings. Also, routinely evaluate how long meetings need to be if you stick to the agenda — can an hour meeting be cut to 30 minutes? Make sure everyone shows up on time, avoid impromptu meetings if possible, and stick to a schedule.
  4. Burnout/stress. Encourage people to have a dedicated workspace in their home and go to it/leave around work hours. Getting dressed/undressed for work also helps establish that boundary by letting people feel like they can disconnect. Encourage people to use vacation (even if staycation) to relax and disconnect. We started strongly encouraging time off in June as we realized that many people had not taken a single day off (and many working weekends as well) since February. It’s striking how much more engaged and productive someone is after a few days off.
  5. Training. Invest the time into good documentation/SOPs/training videos so that people can self-learn. Schedule ongoing training and check-ins over the first few months (even just 30 minutes, two times per week) to give new hires a chance to ask questions, as it is easy to not be heard/seen with everyone remote.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. 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. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

Ensure the expectations and metrics are clear — a team member should know where they stand prior to any conversation. Make sure cameras are on, and be direct but not personal — stick to the facts. We’ve had success with clear targets (accounting closing the month by the 15th of the following month) and weekly dashboards with a baseline you can objectively measure against.

Have corrective conversations early, and give direct feedback continually. If someone starts falling behind, it’s much easier to address in the moment or in a weekly one-on-one than three months down the road.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

Some situations warrant a video or phone call. But if you do feel like a particular piece of feedback is safe to send in email or a chat platform like Slack, lead with or follow up with the fact that you’re happy to hop on a call if needed. Also:

  • Be specific.
  • Criticize in private, praise in public. Make sure you aren’t blowing someone up on a thread with 20 other people.
  • Take the emotion out of it. Don’t be afraid to write an email and wait an hour, day, etc., before sending to make sure it is an accurate reflection of where you are.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

Over-communicate, and be proactive about communication. Have good dashboards and reporting so that everyone can see what is going on. Send those reports out to the group on a regular basis.

Have a project management tool. If you don’t have one, get one (Asana and Trello are great).

Implement greater flexibility. You can’t micromanage people who are at home (if you need to micromanage to begin with, you likely hired wrong, trained wrong, don’t have a strong measurement, or have broader issues). Set clear goals and have good ways to measure, but then give people the ability to hit in their own way. This can apply to work hours; don’t stick to 9–5 if people can get their work done at odd hours. Focus on results over butts in seats.

This ties into flexibility, but working from home is tough for parents when kids are also at home. Be flexible, and allow people to have flex hours. Still hold high expectations, but focus more on “getting things done” vs. “butts in seats from 9 to 5.”

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Turn your cameras on during meetings, schedule social time, set clear, aggressive goals, and celebrate when you hit them. One of our values is Achieve, Celebrate, Iterate. Do great things, acknowledge, repeat.

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. 🙂

Remote life — obviously there are associated challenges, but the potential is huge. Just a few of the ones I personally believe in are:

  • Environmental impacts. We’ve seen cities dramatically cut smog and pollution with less traffic on the road.
  • Time. Commutes suck. The average American spends over 50 minutes per day traveling to and from work. If people did not have to travel to work, on average they would save almost 10 days per year.
  • Improved Cities. We’ve started to see it in New York, Seattle, and Portland, but with fewer cars on the road during rush hour, cities could evolve to be built more around local community, walking, biking, etc. and less around cars.
  • Expenses. Remote work enables us to land jobs based on skill, not where we live. It seriously increases the potential for workers to find the jobs they want, as well as choose a place to live that can afford them the lifestyle they wish to have. This type of setup could also help us cut costs associated with commutes, such as shifting from one car per person to one car per household.
  • Education. What if the quality of education wasn’t limited by the schools in your neighborhood, but you were able to access the best teachers, so long as you had an internet connection?

I could go on and on. We are faced with a huge opportunity if we start thinking about this shift as a wealth of potential vs. a nuisance.

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

“If everything goes according to plan, we didn’t try hard enough.”Have a plan, execute it well, but don’t be afraid to stretch. Your goals should be ambitious enough that you can’t always hit them.

Thank you for these great insights!

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