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Lenwood M. Ross of Accelery: “Humility and empathy go a very long way”

Humility and empathy go a very long way. Pride and self-righteousness will destroy you. If you want to accomplish a vision bigger than yourself, you’ll need to inspire other people to join you on your journey. The lowest form of leadership is authority. If you want to get loyalty and exceptional results as you build […]

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Humility and empathy go a very long way. Pride and self-righteousness will destroy you. If you want to accomplish a vision bigger than yourself, you’ll need to inspire other people to join you on your journey. The lowest form of leadership is authority. If you want to get loyalty and exceptional results as you build your team, operate from a place of humility.


As a part of my series about “Lessons From Inspirational Black Men In Tech,” I had the pleasure of interviewing Lenwood M. Ross, an attorney and family game night afficiando turned entrepreneur, founder, digital transformation expert, coach and CEO. Lenwood trains sellers to accelerate pipeline and meaningful virtual conversations using social media. Lenwood focuses on helping professionals overcome the barriers to successful virtual selling, as well as helping enterprises with more than 50 sales and marketing professionals manage global sales transformation at scale.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I am a lawyer. I practiced in law firms and in-house for 12 years before transitioning to business. I wasn’t as good an attorney as I wanted to be, in part because I had no passion for the work. In my last corporate position, I served as the senior corporate counsel of a publicly-traded retailer. I led our small team. During my tenure, we went through 3 CFOs, an internal investigation of our General Counsel, Founder, and CEO, three financial restatements, nearly went bankrupt. I participated in approximately 250 board and committee meetings — a lifetime of experience in just five years.

After much prayer, I decided that another 25 or 30 years working as a lawyer was not for me. Acting in faith, I walked away from my position. I did not know where my journey would lead me. But I believed that I could achieve my goals and have a more fulfilling life in another career.

I would not recommend that approach, by the way. It would be best if you had more of a plan than I did. It took much longer than I ever imagined to build a new career as an entrepreneur.

Can you share the most interesting story that happened to you since you began at your company?

I’ve had several people work for me over the years. When I first started the company, I wanted more for people than they wanted for themselves. It’s a common leadership mistake. It also leads to disaster. Some people only want to collect a check. I hired a check collector once. Once. It leads to terrible results. Check collectors are apathetic. They do the minimum required to achieve their check collecting goal.

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?

There’s a lot to learn as an entrepreneur. When I began my journey, I had no idea what I was doing. I think many entrepreneurs start the same way. I had a hammer. So everything looked like a nail. I erroneously believed that customers shared my values. That’s a big mistake. Successful entrepreneurs learn how to determine what customers value, and they sell that.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

An entrepreneur’s journey is a lesson in character development. You’re not an entrepreneur until you become one. When I started my journey, I didn’t know that I wasn’t the person that I needed to become to accomplish my goals. The struggle requires you to face your deepest fears and insecurities, overcome self-doubt, ignore naysayers and haters. When you do all of that, and you keep going, you can call yourself an entrepreneur. Every entrepreneur thinks about quitting. You never hear about the entrepreneurs that do.

I have a friend who was a co-founder of a company called Hotjobs back in the late ’90s. Yahoo acquired Hotjobs, and he was out before the Dotcom bubble burst. Retired at 28. We had lunch when I was starting, and he said, “being an entrepreneur is an enriching journey and more challenging than you can imagine.” It was a warning as much as encouragement.

For most, it takes years of failure to get that big win. The big win can’t be your measure of success, however. The big win is the result of micro-successes along the way. Those are the wins you measure because it’s going to take micro-successes to get that big win.

The big names aren’t the best examples. You know the characters, Peter Thiel, Mark Zuckerberg, Jeff Bezos, Elon Musk, Mark Cuban. They are all entrepreneurs that achieved extraordinary results; but, their big wins are atypical. I am confident that each of them would tell you to focus on daily successes. That’s what will give you the fuel to get the next one.

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 about that?

I could thank many people that helped along the way. But I haven’t had that one mentor who made a difference. I have been aided most by studying leadership from John Maxwell and Michael Hyatt. I have also learned entrepreneurship from Steve Blank, Eric Reis, Alex Osterwalder, and Yves Pigneur.

The most significant help to me came from observing leaders along the way. Crisis tests leadership. I failed many times as a leader during those five years. Failures are the best lessons. I knew I had to improve my leadership in every way to achieve my goals.

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

I read The Effective Executive by Peter Drucker a couple of years ago. It’s one of the most important books that I have ever read. In the book, Drucker lists eight practices that an effective executive must make habits. At the end of the list, he throws in a 9th practice that is so important that he calls it “a rule” for all influential executives, “Listen first, speak last.”

I learned this lesson the hard way. Listening to understand what people are attempting to communicate and why they are sharing is mission-critical. If you want strong collaborators on your team, people must have sufficient space to speak and comfort that you will hear them.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. The United States is currently facing a very important self-reckoning about Race, diversity, equality, and inclusion. This is of course a huge topic. But briefly, can you share your view on how this crisis inexorably evolved to the boiling point that it’s at now?

Slavery is this nation’s original sin. The Founders’ decisions wove Race into its fabric. The descendants of enslaved people today continue to suffer the consequences of slavery. More importantly, the philosophy of white supremacy and its codification in the nation’s laws permeates the culture. It is not clear to me that people have abandoned white supremacy. Although I experience the effects of racism, white supremacy is the root cause. White supremacy is about white identity. Racism is not a black person’s issue.

Millions in the United States don’t think about racism, ever. Yet millions experience discrimination every day. That is why we have a crisis in this country. Until the millions who have the luxury of never thinking about racism make it their business to abandon white supremacy, Race will continue to be an issue.

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Diversity exposes us to different perspectives. Ultimately, our decisions are nothing more than judgments. Input from people of different backgrounds and life experiences helps the CEO make better decisions. That’s increasingly important in our global business environment. It does no good to have a diverse executive team just for diversity’s sake. CEOs must value different perspectives.

People create limiting beliefs. If a female job candidate sees no women in senior management, she will believe that women can not reach senior management. She will choose to take a job at a firm that doesn’t have the same apparent limitations.

Diversity in the executive team sets an example. In today’s hyper-competitive environment, there is no room for dead weight. A diverse executive team impresses recruits and junior associates that there are no arbitrary limitations on their advancement opportunities.

Let’s zoom out a bit and talk in more broad terms. It’s hard to be satisfied with the status quo regarding Black Men in Tech leadership. What specific changes do you think are needed to change the status quo?

There needs to be intentionality. That’s it. Business leaders know how to set goals, create KPIs, measure results, and reward performance. Executives are not born; companies identify them and invest in them. Reject the notion that the white candidates for anything are superior.

We’d now love to learn a bit about your company. What is the pain point that your company is helping to address?

We train professionals to use social media for virtual networking and relationship building. Networking and relationship building is mission-critical for B2B sales. Most professionals relied on conferences and in-person events to get access to new clients and have conversations. The pandemic ended that, and we’re not going back.

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

There are a few things that separate us from our competition.

The first relates to how we approach marketing. We believe that traditional marketing is broken. We see evidence that buyers have changed fundamentally, which has caused a paradigm shift in marketing. Buyers now have all the power. In the B2C market, we have seen brands use influencer marketing on social media sites, like Instagram and Tik Tok, to take advantage of this shift. Access to the supply of almost anything is limitless, including knowledge workers like lawyers and consultants. So, we now see the rise of micro-influencers in the B2B market. I wrote an article on LinkedIn about it called, “What the Kardashians Can Teach You About Getting Paid.”

We see our competitors using traditional marketing tactics on social media to help clients. They are either teaching their clients to use these tactics or using them on their behalf. It is a transactional approach that destroys the value of the client’s network every day.

LinkedIn recently changed its terms and conditions to address the behavior. If they catch you engaging in specific actions, you will be banned from LinkedIn indefinitely. I can not imagine a more devastating result for a professional.

So, we focus on helping people changing behavior to create a sustainable competitive advantage. Consequently, we achieve better results faster.

Results depend on actions. Therefore, the results vary. Typically, we will see a bell curve. For example, a small group of technology consultants with a managed services provider working through our 12-week training program started the program with an “acceptable” and a “good” goal. They achieved 5x their “good” plan. We’re now planning to scale the program across the enterprise. We can support the training demands of global multinational organizations.

Are you working on any exciting new projects now? How do you think that will help people?

We are very much in start-up mode. So, everything that we do is new and exciting. Last year, we focused on establishing key strategic partnerships. We will continue building our crucial alliances this year; but, there will be much for focus on market development.

People are at the core of what we do. Our mission is to help people adapt to digital technologies. When leaders talk about digital transformation, there is sometimes an overemphasis on technology. When we look for companies leading in business transformation, we see that the leaders focus on developing people. Microsoft is an excellent example of that. If you go back five years, you see that Microsoft was under attack from Google, Salesforce, AWS, Apple, and lagging. When Satya Nadella starts as CEO, you see him focus on changing Microsoft’s culture. In my opinion, that’s the key to their success. I don’t want to oversimplify what they have accomplished; but, none of it would have been possible without creating a digital culture. It’s the people who move the company. Technology is just a tool.

Last year, some thought leaders in digital transformation from Harvard, MIT, and Deloitte released a book called, The Technology Fallacy. I highly recommend it. The authors focus on an often-quoted statistic that 80% of digital transformation initiatives fail. What they conclude is there is too much focus on technology and not enough focus on people. So, we begin with people and build the technology around what they need to make this transformation easier.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill? From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

We work in B2B. We would advise training your team in virtual networking and relationship building right away. Time matters. Learning how to sell virtually is a skill that requires training and coaching. We’re not using Dux-Soup to auto-connect 100 people a day or hiring someone in the Philippines to pretend they’re you on LinkedIn, which is now a violation of LinkedIn’s terms of service.

Most people want to develop their network just as if they joined a BNI group that hosts Friday morning breakfasts once a month. Today, it’s possible to manage a much more extensive network to build relationships through conversations, virtually.

Do you have any advice about how companies can create very high performing sales teams?

I am all for technology. If you want to create a very high performing sales teams, you must address digital maturity. Digital maturity begins with mindset. Carol Dweck’s book Mindset: The New Psychology of Success is a must-read. The bottom line is that people have limiting beliefs. But, they can change those beliefs. When they adopt new liberating truths, their capacity to grow and succeed expands. There can be no business transformation without people transformation.

Gartner, the leading research and advisory firm, predicts that the shift to virtual networking will break traditional sales models over the next five years. Any firm with a desire to survive and thrive needs to invest in training and developing its sales team for modern selling.

In your specific industry, what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

We use the same virtual selling methodology that we train our clients to use. There is no more effective method to build your brand, develop your network, create opportunities for conversations with new clients, and demonstrate your expertise.

The biggest mistake that I see people make in virtual sales is a myopic focus on their buyers. When you think about your network, there are personal contacts, champions, potential buyers, and influencers. We can activate all of these people simultaneously to generate leads rather than focusing solely on your buyers. We’re much more likely to win a deal when someone who knows us recommends us. We can manage this activity on a massive scale with the right tools and know-how.

As an example, I commented on a post by someone in my network last month. A well known organizational psychologist saw my post and invited me to connect. We scheduled a chat a few weeks later. During our conversation, I mentioned Carol Dweck. She said, “Of course, I know Carol.” Carol Dweck is someone that I’d like to know. I now have a contact who can introduce us.

This same approach got me a meeting with a partner in a private equity firm. That meeting has turned into introductions to CEOs of their portfolio companies. Developing your network is about meeting interesting people and having conversations; this is true in person and virtually.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

The best and most important strategy is to understand your customer — customers buy products and services to help them get jobs done. The best way to build your customer experience is to have customers use your product. Observe them and get feedback. Focus on what they do more than what they say. Unless you are using freemium pricing strategies as part of your platform development, charge your customers. If your proposed market is unwilling to pay to use your product, the need for your product may not be strong enough, or the value proposition may be insufficient.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

I have lost customers before; but, we’re not far enough in our development to experience significant churn.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

We are an early-stage company. So I will speak to what I know as an entrepreneur who has managed to form meaningful strategic partnerships with companies more mature than my own and get some early traction. I have also failed enough to know the difference between failure and success.

First, you’re not an entrepreneur until you become one. Entrepreneurship is a journey. When I started walking this path, I was a bit naïve. Saying you’re an entrepreneur doesn’t make you an entrepreneur, and neither does getting funded. You have to experience becoming an entrepreneur. It breaks you down and builds you back up. Most people quit on the way down. Those who persevere get the rewards. You know that you’d do it without getting paid when you’re not getting paid, and you keep going.

Second, your leadership skills are the lid on your business. Want to go to the next level? Raise your lid. When I started, I struggled with productivity. I had to learn how to be more productive at each stage of our development. Our team follows the same strategies, tactics, and tools to stay focused and move the business forward.

Third, humility and empathy go a very long way. Pride and self-righteousness will destroy you. If you want to accomplish a vision bigger than yourself, you’ll need to inspire other people to join you on your journey. The lowest form of leadership is authority. If you want to get loyalty and exceptional results as you build your team, operate from a place of humility.

I worked very closely with the founder of a billion-dollar retailer. He was always thanking people. The people who worked for him were exceptionally loyal and diligent. I didn’t understand the connection between those things until leading my team. Your people will move mountains when you respect their contributions and thank them.

Fourth, systems help you scale your business. You need them. When you’re building a company, you should know your motivation and have an exit strategy. If you’re building a lifestyle business, that may be less important than building a legacy business. If you plan to sell your business, buyers want that business to run without you. You will need systems and processes to get to that point.

Fifth, allocate your time and energy to the day’s most important tasks. I plan my day to accomplish no more than three significant tasks to move my week’s goals forward. You can’t focus on more than that and be effective. If you do that consistently, you will achieve your goals very quickly.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous 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. 🙂

The United States is a great country that still has enormous potential. I am concerned that our political system no longer works for the people. Politicians are more concerned about their reelection than accomplishing anything for the American people. That’s a significant problem. Our influence around the world is on the decline; and, China’s is rising. We’ve got to change that. We can not afford to waste time looking back on a bygone era. We must look forward to the future. Our greatest asset, the American people, perish for lack of vision. We need significant reforms in campaign finance, media, criminal justice, healthcare, and taxation to get this economy working toward the common good.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them 🙂

I’d love to talk with Brené Brown. Her work on leadership is so important to the business transformation so many organizations seek. Where business transactions are increasingly digitized and social media platforms have hundreds of millions of people, who we are, our character and experiences, is the only thing that makes us unique. People have a tendency to hide behind titles and status. Inevitably, these pretenses deveop in response to insecurities, rejections and humiliations that would us and make our hearts callous. I had to address many of these issues to unlock my fullest potential.

Brené Brown is doing great work to help people overcome these challenge to be the courageous leaders that we need them to be.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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