Team

Not to Lose

Whether it was traveling with the teams my dad coached as a kid, playing club soccer at an early age, monopolizing my time in high school, playing all through college, or being the focus of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. I’ve since shifted toward the more secret exercise of golf, but memories remain, and sports have so many playful metaphors.

Sports and other organized activities help us push to be our best, and the sense of belonging is the real magic.

No matter the sport, it can be easy to get ahead before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early advantage, it’s natural to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation, and the added pressure often leads to the opposing squad scoring an equalizing goal. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then just hoping everyone can work together. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few ways we get ahead, then play to lose, but many leaders are lulled into this trap.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then maintain pressure and stay on the offensive by leaning into the pain.

As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with more initiative to keep playing beyond the fear of losing.

Brewed From Within
📖 Entrepreneurship

By Ben McDougal, ago

Reluctance

There’s an art to keeping the right people engaged for the right amount of time. When things feel stale, it’s a signal of disinclination. To infuse new energies into a group, create space by releasing the reluctant.

Life happens, so it’s natural for interest and commitment levels to change over time. While engagement may expand, anyone’s ability to contribute can just as easily be reduced as transition occurs, missions evolve, and roles transform.

The spiral of someone’s reluctance will soon create stress between others who are still devoted. The longer this misalignment lingers, the more tension it creates.

Even so, people hold on too long, and most of us choose to avoid confrontation. This extends the pain for everyone. The reluctant feel guilty for not contributing while the zealous begin to resent the perceived lack of integrity. Stakeholders experience obscure toxicity and less dependably, which devolves into reduced trust, enthusiasm, and engagement.

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“Winners quit all the time. They just quit the right stuff at the right time.” –Seth Godin

Keeping an eye on our personal bandwidth adds clarity for what and when to quit. This self-awareness helps leaders stay centered and motivated by the way we spend our time. It also helps maintain good relationships by avoiding the unnecessary roughness of dramatic encounters, even when it’s time to explore a new direction. When bridges don’t get burned, we can make a ruckus, move on, and actually expand our impact while still staying connected.

For leaders dealing with lingering reluctance, let’s finish with a few friendly tactics to keep a group vibrant, while maintaining lasting loyalty from the departed.

Start by respectfully inviting individuals who have written their story to graduate gracefully. Sometimes, good people simply don’t want to quit on the people or program they care about. If time has been committed or someone’s identity as a leader is closely connected to their position, the transitional period takes more time, and the group will need to show proactive initiative to prove they are ready to lead without the departing individual. Rarely is there a perfect time to step down, but when given a polite opportunity to exit with elegance, appreciation leads to smooth transitions.

Another way is to ask everyone to do more. Inviting initiative provokes less committed members to bail. The danger is that you may lose others who may not like being asked to go beyond the original game plan.

Lastly, recognize the end will always come. Be clear with expectations, transparent as things evolve, and keep succession a part of ongoing planning.

Along with being open up front, complement internal clarity with external celebration. Acknowledge individuals who made a difference in the past, and praise those who are being generous now. This nurtures an environment where people are inspired to do their best when they’re involved, without feeling a sense of loss when it’s time to let go.

Brewed From Within
#54 📖 Leadership

By Ben McDougal, ago

Ask For Help

I was raised to “go figure it out”.

This DIY mindset was reinforced through years of education and employment in traditional, corporate environments. If there was a problem that I didn’t have the answer to, I would naturally slide into problem solving mode to independently determine different ways to ensure progress. By and large, this mindset has served me well. It has taught me to be resilient in the face of challenges, even when it’s not the popular path forward. It’s left me with an open, achievement-oriented approach with less limitations, because I am a DIY business woman.

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This caffeinated contribution was written by Laurie Brown. I had the pleasure of collaborating with this operational savant through her work inside the Kauffman Foundation and with 1 Million Cups. Laurie is now helping fellow founders optimize their own business operations, so let me know if you’d like a warm introduction.

Lately, I’ve been re-thinking this approach. Perhaps my DIY mindset should include more asking for help?

Within a recent career transition, I’ve been exploring this new attitude through an experiment. On numerous occasions, I’ve encountered unknowns. In these moments of uncertainty, I’ve resisted my life-long instinct to figure out every answer on my own. Instead, I have started asking myself, who in my network might be able to help me learn?  As this experiment has unfolded, I have three key takeaways.

  1. Asking for help drives results. I can learn from others who have pioneered effective solutions, which saves me time (and pain) along the way.
  2. The collaboration from these exchanges go beyond the problem at hand. Many times it strengthens relationships, the fun of helping each other forms friendships, and mutual professional growth is a welcomed side effect.
  3. By leading the way to ask for help, I serve as a role model to my peers and open the door from them to ask me for help in return.

My DIY ways will continue to serve me well, but I’ve learned that an added dose of curiosity and willingness to listen can add fresh layers of potential. I’ll continue to carry forward my resilient, solution-driven approach, but plan to incorporate more inclusive problem solving and an “AFH attitude” within my engaged network. This will keep problems from staying problems, while also creating a new catalyst for prosperity.

By Ben McDougal, ago

Winding Whys

Asking “why” seems to be innate.

As soon as kids learn to speak, the inquisitions begin. The first few whys may emerge from innocent curiosity, but it’s easy to tell when the game is underway.

It’s easy to see how endless whys may lead to frustration (especially when it’s bed time, eh), but I’ve found joy in making these winding whys into a fun challenge for myself. Instead of shutting things down, I enjoy trying to quickly answer every why with an accurate answer. Can I mindfully outlast the youngster’s attention span? What fun!

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I’ve enjoyed winding whys many times, but “Dad, why do you love me?” gave me pause. I found myself feeling appreciative as I tried to coalesce endless reasons into one answer.

As I poked around, it felt trite to reflect on how humans have so many whys we can not answer. Instead of going down the paradoxical path or leaning into understanding our own whys, I found the Five whys interesting.

Developed by system thinkers inside Toyota back in the 1980’s, this iterative Five whys technique was used to explore the cause-and-effect relationships underlying a particular problem. When following 14 specific rules, after exactly five whys, the last answer often points to a process that is not working well or does not exist. This rigid technique has critics and would seemingly lead to shortsighted interpretations, but it was fun learning about this historic use of why. Knowing the value of complexity vs. simplification, as well as, so many other methods like active listening, Socratic questioning, casual diagrams, storytelling, inverse charisma, and pure wonder, the Five whys may not answer all the winding whys of our world, but perhaps it’s another tactic to throw in the mix.

Why not?

By Ben McDougal, ago

Celebrate

Celebrate small wins, mini moments, and game-changing achievements. This reminds everyone how fun it is to be successful. Celebrating also recharges the intoxication that comes with building things that matter. This makes people more eager to tackle new challenges, so do it often. With a connected collection of diversified milestones to keep everyone united, accountable, and motivated, here are a few easy things to celebrate.

– New Hires
– Work Anniversaries
– Product Releases
– Fresh Features
– Customer Testimonials
– Record-Breaking Activities
– Community Gatherings
– Media Spotlights
– Industry Awards
– Event Highlights
– Holidays
– Failures

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Working to establish a few cool milestones and creative ways to celebrate them? Here’s an NFT to unlock some time together!

Most companies love to celebrate together, but too much of a good thing can lead to unnecessary drama. In contrast, when there aren’t enough good times, the team forgets how to have fun as a team. To stay equitable, listen and learn how different people respond to business breakthroughs. As you consider what and ways to celebrate, invite everyone into the activity planning process. Milestones may not change, but the way you celebrate them sure can. Connecting achievements with inclusive celebrations will motivate everyone, while also infusing a freshness into the mix.

As we celebrate in style, the entire team is supported by a performance-based culture where everyone feels included and has fun building as one.

By Ben McDougal, ago