“Communicate Honestly” with Tim Singleton

Communicate Honestly — Turbulent times are when people want to follow someone they trust and respect. Leaders that speak to difficulties with real solutions, with candor, and without shying away from the problems will win both trust and respect. As part of my series about the “Five Things You Need To Be A Highly Effective […]

Thrive invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive or its employees. More information on our Community guidelines is available here.

Communicate Honestly — Turbulent times are when people want to follow someone they trust and respect. Leaders that speak to difficulties with real solutions, with candor, and without shying away from the problems will win both trust and respect.

As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, I had the pleasure of interviewing Tim Singleton.

Tim has worked in the computer and technology industry since 1999, doing everything from entry level help desk work to designing business networks and advising large IT organizations. He currently owns and operates Strive Technology Consulting, a managed IT service provider near Denver, providing enterprise-class support and guidance to small businesses.

Thank you so much for your time! I know that you are a very busy person. 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?

Thanks for the opportunity, Jason.

While I was in college, I was fortunate to become friends with a group of guys that were interested in computers and technology and I really got into it. I learned so much and to this day, they are some of the smartest people I’ve ever met. That lead me into my tech career, and I discovered I had a great natural talent for it. I worked for several years in the venture capital world in Boston managing IT networks before deciding to get away from the city life. I moved to Boulder, Colorado where I started my own IT consulting company, Strive Technology Consulting. Meanwhile, I started getting trained in leadership skills through the lens of inter-personal relationships, which I still practice and teach, in addition to running Strive.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

It’s funny now that I know better. When I first came out here, I thought, “I’ve been doing all the IT work for these companies for years. I can do this on my own. All I need is a few clients and everything will be great.” Anyone who has started a business gets the joke already. I was assuming the IT was the hard part and I had already mastered that. In reality, “All I need is a few clients” was the hard part. The big take-away is that all organizations, no matter how mission-driven, must be sales-focused organizations, or they can’t get their mission accomplished.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Early in my career, I befriended a man at the tail end of his. He talked to me about business and people in the industry in a way nobody else had. He taught me that everything around us was just made by some ordinary person that decided to create something. And through him, I realized that I had just as much a right to impact the world around me as any of them, and the talent to get it done.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

I grew up in the ‘80’s being inundated by examples of corporate greed, misbehavior, and excess. I also grew up seeing my father run his small business where people enjoyed each other and enjoyed their work. When I started my company, I strove to create a shining example for the world. I wanted to show people that businesses could treat everyone involved with such dignity, respect, and care that everyone would want to do business with them and they can be successful, profitable because of that ethic, not in spite of it.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

I pay a lot of attention to the personal level. When Coronavirus first started affecting everything, I had a meeting and led an open discussion about what was happening, what people were concerned about, how we were seeing the situation, and how we were planning to address it. The goal was not to impart information, just to let everyone know we were listening, cared about them as individuals, and were going to keep leading. We sent everyone to work from home early on and started frequent video calls to re-introduce personal connection and mentoring.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

To be honest, I consider giving up a couple times a year. Life would be so much easier if I just got a job and let someone else deal with all the stress. But the company’s vision really inspires me, and I want to be a part of what it would bring to the world. When I really consider my options, I wouldn’t want to be at any company other than the one I’m trying to build, so I stay and continue building.

What would you say is the most critical role of a leader during challenging times?

Be the adult in the room. Make a lot of plans and communicate abundantly. There was so much panic when the pandemic started because so few people were saying, “here’s what we know, here’s what we don’t know, here’s what we’ll do. We’ll give you an update tomorrow.” In challenging times, people want to be led, so lead them. Specifically, game out possible futures, create a plan for each of those, and work to keep lines of communication flowing strongly in all directions. Talk to people a lot more than usual, be direct and honest, and let them know that you are taking the lead.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

Help other people.

When we face hardship, humans tend to band together and help one another. We actually do this far more than we take everything we can for ourselves. People want to help each other in uncertain times. In our businesses, we are all doing something for the good of others, or else they wouldn’t buy our products. Zoom way in on the good you are doing and how you can use your resources to help others out. There is nothing that boots morale more than this.

What is the best way to communicate difficult news to one’s team and customers?

Speak honestly, speak directly, and stay in relationship during the conversation. We often sugar-coat bad news, or drop it like a bomb and walk away because it’s hard for us to witness the impact it has on the other person. Don’t do that. Give them the respect of speaking candidly and honestly. Be compassionate if the news is hard for them to hear. And let them have whatever reaction they have without defending yourself. If you’ve made the decision with integrity, then you haven’t done anything wrong; it’s just hard. Stay with them through that. If they get angry and lash out, that’s on them — you’ve done what must be done and tended to the relationship.

How can a leader make plans when the future is so unpredictable?

That’s the wrong way of thinking about it. Plans are what make the future predictable. We look around and try to figure out what the environment will look like in the future. Then we make plans for how to thrive in that environment. In rapidly changing environments, our plans may be incorrect, but that just means we need to plan more. Normally, the environment of the next few months will look a lot like it does today. We are not in normal times. That just means we spend more time imagining possible future environments and planning for each of those. Yes, you will throw most of your plans away, but when the future shows up and it looks like a possibility you planned for, you know how to proceed.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

“Be more helpful, not less.” Turbulent times are stressful. Humans have three responses to stress: fight, flight, freeze. When leaders (and in turn, their companies) go into a flee or freeze response, their employees and customers feel abandoned at a time when they really need more help and leadership. Manage your stress or channel your fighting instinct and pitch in. In whatever capacity you have as a person, with whatever resources your company has, be more helpful to everyone you can reach, not less.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

Businesses often stop their sales and marketing process. Times are different, so they pause normal operations. We all need to continue reaching out to customers, vendors, and prospects. Let them know you’re still there, you’re still trying to serve them, and that times are tough so no one quite knows what that will look like.

A related mistake I’ve seen is when companies continue marketing like nothing has changed. Keep up communications but adjust them for the times. Be attuned to your customers and send out messages such as, “Here is how we’re helping,” rather than, “buy from us.”

A third mistake I see, and one of the most tragic, is companies hiding too much information from their customers and employees. They want to paint a rosy picture of a situation and the future, so they hide problems. In difficult times, you want to communicate more, not less. Be candid, take responsibility, tell everyone you have a plan. That’s what builds the trust that will makes people stay with you through the difficulties — not optimistic stories that most people see through.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

We looked at our offering and our strengths and asked what different things we could offer to the new environment. IT security is a bigger threat now than ever before, especially because of the pandemic, so we started offering more IT security plans to our clients. We also broadened our customer base to include our clients’ employees at home. They were at greater risk working from home, and we had never addressed that issue or market before. We were also able to swap out some vendors that we had been with for a long time for newer, less expensive alternatives.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

  1. Communicate More — We started having team huddles 3 times per day when we moved to work-from-home. It helped keep everyone engaged and feeling like we were all in this together.
  2. Communicate Honestly — Turbulent times are when people want to follow someone they trust and respect. Leaders that speak to difficulties with real solutions, with candor, and without shying away from the problems will win both trust and respect.
  3. Continue Marketing (and don’t be tone deaf) — We ramped up our email communications significantly during the early days of Coronavirus — none of it with a sales pitch. We were sending around hand washing tips, financial guidance, security alerts, everything we could think of that would be helpful for business to know and that they hadn’t been hearing. We curated a lot of it to ensure it was high quality and not the “relevant but not useful” stuff that people were getting so much of
  4. Plan More — In gaming out possible futures, I questioned what would happen if our clients shut down and considered expanding our IT service to residential customers. I planned out several ways that might go and didn’t like any of them. The environment changed and our customers all survived. Now I’m re-working some of those plans and limiting it to home offices and professionals working from home. This is far more promising than before, but only happened because of that earlier “failed” plan. The act of planning helps prepare you for the future, no matter if your plans succeed or fail. As Eisenhower said, “Plans are worthless, but planning is everything.”
  5. Show Your Humanity — I was leading a community through a turbulent time a few years ago and I thought I was supposed to be “The Leader” who stood above the fray and carved the path ahead. It was disastrous. There was dissention, anger, distrust, and more questioning of my role than ever before. When I came down off the high horse and had an honest discussion with the community members, showing my vulnerability and revealing how deeply the situation impacted me, things turned around. When I showed my humanity, everyone else responded to me with more humanity. Without fail, every time I try to rise above the hard times and lead from “above it all,” I fall flat. The more I show my humanity, the more I am responded to with humanity. Yes, it is a fine line to walk in showing vulnerability while not making excuses and appearing incompetent, but it is a skill well worth developing.

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

Lately, this quote from Buckminster Fuller has been inspiring me: “What is my job on the planet? What is it that needs doing, that I know something about, that probably won’t happen unless I take responsibility for it?” I tend to assume everyone knows as well as I do, and others will do the work if I don’t. This quote reminds me that if I don’t do the thing I’m uniquely suited for, the world actually misses out on the unique flavor I bring to the things I do. It helps me continue creating, despite the troubled times I find myself in.

How can our readers further follow your work?

Strive Technology Consulting: WebsiteTwitterFacebookLinkedIn

Personal: LinkedIn

Communications & Emotional Intelligence Training: WebsiteTwitterFacebook

Thank you so much for sharing these important insights. We wish you continued success and good health!

Thanks for having me, I really enjoyed it!

You might also like...


Lisa Swift-Young On How To Leave a Lasting Legacy With a Successful & Effective Nonprofit Organization

by Karen Mangia

“Take some time for your own intentional “airplane mode” to stay balanced.” With Charlie Katz & Peter Polizzi

by Charlie Katz

Meg Daly On How To Leave a Lasting Legacy With a Successful & Effective Nonprofit Organization

by Karen Mangia
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.