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What's Your 2020 Hindsight?

What's Your 2020 Hindsight?

January 31, 2021

So the saying goes, “hindsight is 20/20” and now we can finally say just that. With “the year 2020”  in our rear view mirror, there’s a lot to look back on.

In January 2020, business teams around the world held in-person meetings to set out company goals, KPIs and deadlines for the year ahead. By March, accountability measures were quickly scrapped for Personal Protection Equipment (PPE) and remote working solutions as companies scrambled to navigate the turmoil of a rapidly unfolding global pandemic.

Now one year later, many of us have forgotten to take a moment to see the glistening moments in all of that rubble. There were more than you might realize if you take time to pause and reflect.

Top 5 Questions for 2020 Perspective

In acknowledgement of all that 2020 took from us – AND in celebration all that it gave us – here are five thought-provoking questions to ask your team. As food for thought, we had our team answer these questions, too. Check out what we learned by reflecting back.

  1. What was the single best decision you made as a company in 2020?

When we took a crack at this one, the answer came to all team members very quickly. Amidst the scariest months of the pandemic, we pulled the trigger on a decision to launch our very own podcast. With loads of grit and a few helping hands in the family-business world, the Family Biz Show podcast has been a major success. Since May we’re happy to celebrate the launch of over 20 episodes with many more in production!

We have also added on a quarterly Book Club. This forum allows us to connect our clients and the larger business community to some of the smartest thought leaders in the realm of family and business, so we can grow smarter – together.

  1. What did you think was IMPOSSIBLE at the beginning of 2020, that your company proved POSSIBLE by the close of business New Year’s Eve?

For us it was growth. 2020 was slated to be a great year in business for Family Wealth & Legacy.  A client was poised to have us officiate the sale of their business at the beginning of the year, which would result in big revenues. While the sale did get completed, it happened much later than originally anticipated. This delay created apprehension and uncertainty. It also made us realize that we didn’t have any solid new prospects on the radar, so looking beyond 2020 conjured scenes that appeared more like an ominous cloud than a bright future.

This uncertainty prompted us to pull the trigger on two things we had been avoiding: Sales and Marketing.

Like many small businesses, we had great marketing ideas. We talked about them all the time, but we didn’t have the systems in place to make it happen or deliver them with any level of consistency. So we embraced the reality that we needed a marketing plan and that meant hiring an outside party to help us do it. It was the kick we needed to get outside of our comfort zone, and make the previously “impossible” possible. We coupled that stronger branding and marketing strategy with hiring a sales coach to build a clear sales process for the team.

So, what unthinkables did your team implement in 2020 that made your impossible, possible?

  1. How did your team live out the company core values in your business, and in your community?

We had a hard time taking a moment to celebrate this one. It wasn’t that we hadn’t lived out our core values throughout. We had. Every team member had completed new trainings. Every team member had come to the table with egg on their face when warranted. Every team member had stayed humbly accountable. But this question is best answered in the minute moments of our daily work-lives as teammates.

In 2021, we’re making the celebration of our core values a bigger priority. Before each quarterly team meeting, every team member is asked to complete a brief survey on our core values. They detail exemplary moments in their work life and/or personal life that they feel really captured that particular core value. Team members who complete the survey and present their findings at the quarterly meeting are entered into a raffle to win a prize. It’s a true win-win and culture builder.

  1. In what ways did you serve your clients better than you did in previous years?

Though there were signs that our industry would be making integral shifts into the virtual world in the coming decades, as a team we couldn’t fathom ways to keep tight-knit bonds with our clients without quality, in-person interactions. Our senior partner spent many Tuesday and Thursdays driving 2 hours away for a full day of meetings to arrive home at 8PM just to make sure all of our clients saw us in person. The thought of working 100% virtually with clients seemed like more of a wild speculation than an innovative idea to us.

2020 forced us to embrace change. The blessing in disguise of 2020 is that our clients were going through integral changes themselves, and it allowed a safe space to finally make the shift. We found ways to continue bonding with our clients virtually still. The frequency of our client interactions have increased significantly. From one-on-one check-ins, to quarterly market update videos right in clients’ inboxes, to virtual client events just to socialize – we’re finding ways to grow closer with our clients every day.

  1. Looking down from a view of 30,000 feet, what advice would you give your “last-year-self” as a leader of your company?

*que crickets chirping*… this is a tough one.

If 2020 personally taught me anything, it was the importance of intentionality. The societal hustle and bustle left me rushing from home, to work, to chores, to exercising, to socialization to long-awaited (and often too short) breaks from the daily grind. The mandatory quarantine forced me to take a look at my life and sort out the important daily tasks from the unimportant – in business and in life.

For me, separating the shaft from the wheat meant weeding out the daily minutiae that comes with being a family business consultant, and pouring some of that raw energy into developing processes to reach more of the community, and better serve our current clients during an ever-polarizing time. My “advice to me” is… before I start a new project or idea, to take a moment and sit...breathe…and make a conscious decision to ask myself, “is this something that will truly help me grow? And will it help the business grow?,”  This simple process helps me to then choose to implement it OR throw it away. Intentionality is power.

So, there you have it. Five simple questions to help you and your team take a moment to pause, breathe, and be more intentional in the year ahead. We encourage you to share this exercise with your team. It’s sure to bring some great conversation to the table.

If you want to know more, you can connect with me on LinkedIn, or email me at We look forward to sharing more with you, your family, and your business.


Kay Pfleghardt is a registered representative of Lincoln Financial Advisors Corp., a broker/dealer (member SIPC) and registered investment advisor. Family Wealth & Legacy, LLC is not an affiliate of Lincoln Financial Advisors Corp. CRN-3425059-012721