Many of us have been in situations where we’re managing a project or advancing a new initiative at work and the leaders supervising the work get lost in unnecessary details. How do you manage up so the project doesn’t lose momentum? Using a real-life scenario of how a director at a tech company built a propensity model to streamline sales and presented it to his leaders as well as the salespeople using it, the authors present three strategies to get leaders out of the weeds on a project: 1) Work with your “users,” 2) sell the big picture, and 3) create self-service content.
Amidst high growth, the salespeople at a global technology company were confused about which accounts and opportunities to focus on. Mark, a rising director on the go-to-market team, was leading a project to build a propensity model to solve this problem. The model took in numerous data points across disparate systems to give salespeople directional leads. Leaders were excited about the model and the problem it would solve, but they often ended up getting stuck in the details during presentations. Mark was beginning to get frustrated. How can he get his leaders out of the weeds so he can keep advancing this important work?
Individuals at all levels in organizations will encounter situations where leaders lose the big picture. We have encountered it across our careers, from starting out when we worked with our bosses on small projects and later, when we presented to boards on transformational programs. While the particular questions in those situations were different, the underlying challenge remained the same. Based on over 30 years of influencing leadership decisions, we recommend three steps that individuals can take to reset the conversation with leaders. We’ll demonstrate these steps with a real-life example of how Mark, a rising director in a $10 billion global technology company, successfully advanced his work amidst a cascade of detailed questions.
When talking with salespeople, Mark kept hearing the same thing: “I don’t know where to focus.” Most salespeople had dozens of accounts, and the company sold a range of products with new releases coming out monthly, meaning some felt overwhelmed by what they had to sell. As a result, the company’s sales pipeline was not developing in line with expectations, and the leadership was beginning to get nervous.
Mark had been at the company for over a year and had just been promoted. He had the internal support and desire to take on a big problem, and he excitedly thought this was it. Working with a data scientist, Mark overcame significant technical challenges, quickly building a dashboard that clearly showed salespeople where the opportunities were in their territories. Salespeople were enthusiastic when the dashboard was released on a small scale, and leaders wanted to hear more. The meetings quickly became a drag though, as many leaders focused on adoption data (one of the data types used in the model) and systems issues, as the company had numerous reporting tools. Their concerns were valid, but Mark didn’t believe that necessitated stopping the work. Disappointed with how the situation was unfolding, he resolved to change tactics.
After a wave of internal meetings with leaders, Mark adopted a three-pronged approach. We’ve found that these tactics work in many circumstances when leaders get stuck.
1. Work with your “users.”
Individuals must think of themselves as product managers, treat their work as a “product,” and move with their users. The leaders who get stuck in the details are rarely the ultimate users of the work. Individuals should continue to work with users, taking in requirements, making updates, and demonstrating value. The lack of full leadership buy-in should not be an impediment. Rather, leaders will be more supportive when there is strong enthusiasm from the actual users.
In Mark’s case, though he was presenting to leadership, the users of his work were in sales. Mark decided to keep working with salespeople to understand what they liked about the dashboard and what should be improved, just as if he was a product manager. He kept developing the tool based on their feedback. In addition, when he gave enablement trainings to sales or was in meetings with leaders, he had salespeople present with him. This positive feedback demonstrated to leaders the value of the project and led to them spending more time considering how to scale the work and less time questioning the data nuances.
2. Sell the big picture.
When presenting, project leaders sometimes resort to talking about the work in a project management context where they’ll assume buy-in to the vision and then jump into execution aspects, sharing GANNT charts and discussing roles and responsibilities. This is a mistake. Individuals should instead paint a picture of how the work will solve a pressing problem by discussing the vision and use cases, and tying the work to leadership’s priorities.
After some initial discussions with leaders, Mark created a separate presentation for them. The presentation focused on how the tool would make salespeople’s’ lives easier, which would improve pipeline, increase employee satisfaction, and reduce turnover, a priority for leadership. Mark was still prepared to talk about release schedules and workstream owners, but he never led with those points. The meetings began to go smoother, and the executives were relieved to have an initiative that could help stem the flood of employee departures.
3. Create self-service content.
Project managers should create self-service content that addresses technical questions. If two or more leaders ask the same question, it is a good indication it will come up again. Individuals should prepare simple FAQs, descriptions, or video tutorials that address these issues, and they should publish them in an accessible forum. This will reduce the time they spend responding to the same questions.
The propensity model included data on product adoption, as it was a company priority to monitor client adoption of newer products. Mark realized that leaders were getting stuck on how the adoption data was calculated. He worked with the data scientist and product team to create a page on definitions and another on commonly asked questions about the data, and then he posted them on an internal company site. For more technical audiences, he sent out the self-service content in advance of presentations. Questions from leadership about adoption slowed to a trickle, and Mark was better able to focus the meetings on key items.
Of course, challenges will arise no matter what. Leadership will likely want to make changes to the work or they will want to tie it to other related projects that are also underway. That is just part of working on an important initiative. In Mark’s case, leaders originally wanted Mark to align with other data initiatives that were internal. These initiatives were slow-moving though, and aligning fully with them would have jeopardized his project’s ability to quickly deliver value. As Mark successfully used the three tactics, leadership got on board, and leaders began to tell other project managers to follow his work — not the other way around.
The benefits to overcoming these challenges are significant. The company is better off when this kind of work is implemented, and the team that completes the work will reap the benefits. More importantly though, the individuals on the project will have improved their skills, having overcome internal hurdles and won over leaders in the process. In this case study, change took time. But weeks after deploying these tactics, Mark realized that the tone of these leadership meetings had gradually transitioned from skepticism to excitement. His project’s potential was still not fully realized, but he knew that he had developed a new skillset and that the company’s leaders were on his side.
How to Build Upon the Legacy of Your Family Business — and Make It Your Own
Founded by Henry Ford in 1903, the Ford Motor Company rocketed to success by mass-producing reliable, low-priced automobiles. When Henry’s son, Edsel, took the helm in 1918, he championed a different strategy for a new era. He sought to replace the Model T — iconic but outdated — with a more modern design geared to high-end and foreign markets, and later embraced compromise with labor amid the suffering of the Great Depression.
But Henry could not let go of Ford’s origin story, undermining his son at every turn. The result was declining sales and years of labor strife that left the company on the brink of collapse by the 1940s. It was only the efforts of Edsel’s son, the more forceful Henry Ford II, that saved the auto giant from bankruptcy.
In family enterprise, generational transitions often pit one narrative against another: tradition versus innovation, continuity versus change. Indeed, when older generations craft painstaking succession plans or build elaborate constraints into trusts or shareholder agreements, they are really constructing a story: about the values and life lessons that helped them succeed, and that they hope will do the same for their children. Younger generations, however, must often adapt this narrative to their own goals and values, along with the changing world around them.
Failure to reconcile conflicting narratives can spell ruin for a family business or the waste of a financial legacy, as it nearly did for the Fords. To avoid this fate, families need to think differently about the stories they tell.
The value of critical distance
Conventional wisdom holds that family heritage, like wealth and reputation, “belongs” to the older generation. In this telling, succeeding generations are merely stewards or caretakers. They are given an inheritance or entrusted with the family business — and then charged with not frittering it away or screwing it up. Framed this way, a legacy can feel more like a burden than a gift.
Of course, it’s not as simple as that. Research suggests that younger generations do value their family heritage, especially as a source of traditions more motivating than money alone, and are motivated to preserve it. According to a 2021 survey of 300 Canadian business owners by the Family Enterprise Foundation, nearly 90% of next-generation family business leaders believe it is important to preserve a legacy.
But younger generations also want something more from that heritage: a sense of purpose, a collective identity for the family, the seeds of new entrepreneurial gambits, permission to go their own way. And as our own research shows, next-generation leaders are uniquely positioned to find what they are looking for in the family story.
Older generations often identify closely with the family or the family business, which can actually obstruct key learnings from the past. Eager to protect the family’s reputation, they may downplay scandal or setback rather than learn from it. By contrast, our analysis of 94 family businesses shows that younger generations tend to have more critical distance from the family story. This lets them grapple with its difficult chapters and respond appropriately, whether by making amends for past misdeeds or by reforming business practices going forward. It also frees them to draw insights from their story that can fuel innovation and sustainability.
Legacy as a source of purpose
How, then, can the next generation build on their family legacy while recasting it as their own? Our research and experience suggest four strategies for next-generation leaders.
1. Seek out role models in the family story.
Some next-generation leaders hesitate to embark on risky new ventures outside the traditional scope of the family business. Locating exemplars in the family story can legitimize a new way forward.
One third-generation CEO used this approach to advance his vision for a more sustainable enterprise. Fredo Arias-King, head of Mexican pine resin producer Pinosa Group, had lamented the disappearance of Mexico’s ancient pine forests that threatened both the industry and the communities that depend on it. Then he stumbled onto the published speeches of his grandfather, company founder José Antonio Arias Álvarez, who had preached environmental stewardship. “I don’t think he could have known just how devastated the forest would eventually become,” said Arias-King, “but somehow my grandfather knew that planting trees would become extremely important.”
Affirmed by his grandfather’s words, Arias-King helped found Ejido Verde, a nonprofit that would later become an independent, for-profit enterprise. By making no-interest loans to farmers and communities, with pine resin as the means of repayment, the organization promotes reforesting through new pine plantations.
2. Forge an identity beyond the founder-entrepreneur.
It’s easy to revere the family’s wealth creator. For the two adult grandchildren of one founder-entrepreneur — a private equity pioneer who rose from poverty to become one of America’s richest people — that was the problem. They wanted their own children, beneficiaries of a generation-skipping trust, to know the person behind the legacy that would pass to them. So they engaged one of us (John Seaman) to probe beyond the classic rags-to-riches tale they had heard growing up.
The founder, they learned, was a gifted yet deeply troubled man. This more nuanced understanding enabled the two generations to have a frank conversation about the issues raised by their ancestor’s life: the obligations of a business to its workers and communities; the consequences of untreated mental illness; and the unfair burden often shouldered by women in wealthy families.
This conversation, in turn, led members of the fourth generation, all in their twenties, to rethink their roles in the family enterprise. One set aside her qualms about joining the family business and put herself on a path to succeed her father as president, but with a determination to nudge the company’s private equity portfolio toward impact investing. Another resolved to pursue her own entrepreneurial dreams outside of the business, rooted in progressive values that were in stark contrast with her great-grandfather’s. Still another joined the board of the family foundation, where she helped steer its grant-making toward her generation’s individual passions.
By seeing their founder-entrepreneur in human terms, the family’s younger generation was able to move beyond hero worship to forge their own identities — which promised to make them responsible owners and stewards of their ancestor’s wealth and the business that created it.
3. Reckon with past wrongs to find a new path forward.
Many families have skeletons in the closet — scandal or wrongdoing they have long concealed or downplayed. (Henry Ford’s history of antisemitism and violent confrontations with unions are examples of this.) The willingness to confront these darker chapters, it turns out, can be a powerful motivation.
That was the case for the Reimann family, owners of consumer goods conglomerate JAB Holding Company and one of Germany’s richest families. The three adult children of Albert Reimann Jr., who ran the company in the 1930s and 1940s, knew they had been born of their father’s affair with an employee, Emilie Landecker. They also knew that Emilie’s Jewish father, Alfred, had been murdered by the Nazis. But it was not until 2019, when they commissioned research on the company, that a more sinister secret emerged: their father and paternal grandfather were themselves ardent believers in Nazi race theory who abused forced laborers.
It was the younger generation — Albert Jr.’s grandchildren — who were most adamant about reckoning with this secret. “When I read of the atrocities…sanctioned by my grandfather, I felt like throwing up,” recalled Martin Reimann. “I cannot claim that I was very interested in politics before…But after what happened, I changed my mind.”
At the insistence of Martin’s generation, the Reimanns paid compensation to former forced laborers and their families. But they did not stop there. They refocused their family foundation on combating antisemitism and strengthening democratic institutions. They also renamed the foundation in honor of Alfred Landecker, making him the narrative driver behind the more fundamental change they sought. Far from an isolated act of corporate atonement, then, this was an attempt by the next generation to use lessons from their family heritage to build a more just future.
4. Leverage the family story as a source of competitive advantage.
For some family business entrepreneurs, the next venture can begin with a step back. So it was for British restaurateurs (and sisters) Helen and Lisa Tse, whose family heritage empowered their rise.
Their grandmother, Lily Kwok, had emigrated from Hong Kong in 1956 and settled in Manchester, where she and her daughter Mabel built one of Britain’s first Chinese restaurants. But the business eventually went bankrupt, the victim of racism and Chinese gangs.
The story might have ended there. Instead, Helen and Lisa picked up the threads of their family narrative and carried it forward. Abandoning successful professional careers, they established their own Manchester restaurant, Sweet Mandarin, in 2004. But the restaurant only took off when Helen published a best-selling memoir about her grandmother. With this narrative platform, the sisters branched out into other endeavors, like cookbooks and cookery classes, tied to their own life stories.
For the Tse sisters, family heritage proved to be a source of competitive advantage. By recovering an immigrant’s tale with universal appeal, they gained acceptance outside of their own ethnic communities. And by situating themselves in an entrepreneurial tradition spanning three generations, they created a sense of longevity that evoked quality and trustworthiness, even as they also innovated new products alongside recipes inherited from their grandmother.
. . .
Family legacy is not a monologue; it’s a dialogue, a collective story that belongs to the whole family. When families think of legacy in these terms, they empower younger generations to harness that story to their own purposes, drawing strength from their elders. Legacy, in short, becomes not a burden but a blessing — one that can help families sustain wealth and purpose long into the future.
Want to Succeed as an Entrepreneur? 14 Traits to Cultivate Now
If you had to choose one trait that you believed was the most necessary in order to succeed as an entrepreneur, what would it be and why? How can aspiring entrepreneurs cultivate it?
These answers are provided by Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most successful young entrepreneurs. YEC members represent nearly every industry, generate billions of dollars in revenue each year, and have created tens of thousands of jobs. Learn more at yec.co.
1. The Ability to Problem-Solve
The one trait I would say is the most important to entrepreneurs is the ability to creatively problem-solve. Sometimes, solutions to business problems aren’t obvious and you have to find an out-of-the-box solution. That can be a real challenge because most people are taught to color within the lines.
You need courage, resolve and strength of character to withstand the ebbs, flows and failures that lead to successful business. The best way to get this is through experience. I’ve seen a lot of young entrepreneurs with more grit than their older counterparts, especially when they had customer service jobs and worked their way up the ladder to experience different seats in the company.
One of the most essential traits an entrepreneur can possess is flexibility. You need to be able to change your approach in response to market conditions, customer feedback and what any partners or investors want at any given time. Being flexible also means looking at “failure” as a signal to make changes rather than as a permanent obstacle.
Aspiring entrepreneurs should be fearless. It’s fear that often prevents you from grabbing new opportunities, as new entrepreneurs are unable to decide what’s best for them or how a particular decision would affect them. Well, you won’t know unless you try. So, be quick with your decisions. Preparedness is great and all, but if you’re afraid to make a move, someone else will — and will likely succeed.
To be successful as an entrepreneur, you need to focus on developing your social skills. When you have strong social skills, it becomes easier for you to build strong relationships with your customers, investors or anyone you think is important to your business. Good social skills make you a better communicator and help you make others feel secure so they connect with you on a deeper level.
One trait you need to succeed as an entrepreneur is determination. You’ll encounter people who don’t like your idea. There will be times when clients or investors reject you. Your first project idea may never see the light of day. You need to have the drive to move past these unfortunate situations if you want to find success.
Decisiveness is the main trait any successful entrepreneur needs to cultivate. From making decisions about the budget or day-to-day communication, maintaining the ability to decide and decide quickly remains imperative. I use mental models like Occam’s razor to run my life. For example, when presented with two options, I choose the simplest and I get a lot of significant work done.
8. A Realistic Mindset
Be realistic! An entrepreneur’s career is full of ups and downs, which are part of the learning process — and that’s a fact. Keeping your feet on the ground will save you much frustration when things don’t go the way you want. Instead, learn your lessons and keep moving. This will also help you to consider and prepare for multiple scenarios while adjusting along the way.
In order to be an entrepreneur, you must have some moxie. Being outspoken, direct, resilient and having the ability to persevere is something that most entrepreneurs have in common. You have moxie if you can get up after failing. Aspiring entrepreneurs can cultivate it by focusing on confidence. Stand up for what you believe in and don’t let others’ opinions or perceptions get in your way.
10. The Ability to Follow Long-Term Plans
The ability to follow and execute on a long-term plan — meaning multiple years — without being sidetracked by mirages along the way or discouraged by inevitable ups and downs is so important. This requires you to learn multiple skills, including attention to detail, deep work and strategic vision (as opposed to tunnel vision, which trips up many entrepreneurs).
11. A Willingness to Keep Learning
If you want to succeed as an entrepreneur, you should have an open mind toward learning. It’s important for you to realize that learning is an ongoing process. It can help you develop new skills that in turn can help you stay ahead of your competitors at all times.
12. A Self-Reflective Mind
One trait that can help aspiring entrepreneurs succeed is self-reflection. Embracing your mistakes and learning from them is the only way an entrepreneur can grow and be better than ever before. However, one can’t cultivate this skill by enrolling in a particular program. You have to have an open mind, give yourself the freedom to make mistakes and foster the courage to learn from them.
Resilience is one of the most important traits you can develop as an entrepreneur. The journey is going to have high highs and low lows, and it will be your ability to push through and persevere during this time that will be the difference between success and failure. To develop resilience, develop a positive mindset, build a strong support system, understand your purpose and look after yourself.
14. The Ability to Thrive on Ambiguity
The cornerstone of entrepreneurial success is in the ability to accept and thrive on ambiguity. I have found that navigating the unpredictable landscape of business ventures requires you to possess a flexible mindset that can accommodate constant change and capitalize on emerging opportunities. Always stay updated with the latest developments and treat every change as an opportunity to grow.
The Art of Risk-Taking: Lessons from Successful Entrepreneurs
Entrepreneurship is a high-risk endeavor. Starting a new business takes bravery, resilience, and a willingness to accept risks. Many successful entrepreneurs attribute their success to calculated risks and pushing themselves outside their comfort zones.
In this article, we will explore the art of risk-taking and the lessons we can learn from successful entrepreneurs.
1. Understand the Importance of Risk-Taking
Taking risks is an essential component of entrepreneurship. It is tough to develop and produce anything new without taking risks. Risk-taking is necessary for growth and progress, as successful entrepreneurs recognize. They also recognize that not every risk will pay off, but the potential rewards make the effort worthwhile.
2. Do Your Research
Before taking any risks, it is important to do your research. Successful entrepreneurs understand the importance of gathering as much information as possible before making a decision. This includes researching the market, competition, and potential customers. By doing your research, you can make informed decisions and minimize your risks.
3. Network Effectively
Networking is an essential part of entrepreneurship. Successful entrepreneurs understand the importance of building relationships with potential investors, customers, and other entrepreneurs. They attend events and conferences, participate in industry groups, and use social media to expand their network and create new opportunities.
4. Stay Committed
Entrepreneurship is a long and challenging journey. Successful entrepreneurs understand the importance of staying committed to their goals and vision, even when faced with obstacles and setbacks. They stay focused on their end goal and are willing to put in the time and effort necessary to achieve it.
5. Collaborate with Others
Entrepreneurship is often a team effort. Successful entrepreneurs understand the value of collaborating with others and building strong partnerships. They seek out individuals who bring complementary skills and expertise to the table and work together to achieve a shared vision.
6. Surround Yourself with Supportive People
Entrepreneurship can be a lonely journey. It is important to surround yourself with supportive people who believe in you and your vision. Successful entrepreneurs understand the value of having a support system and seek out mentors, advisors, and other entrepreneurs who can offer guidance and encouragement.
7. Set Realistic Goals
Taking risks is essential for entrepreneurship, but it is important to set realistic goals. Successful entrepreneurs understand the importance of setting achievable goals and breaking them down into smaller, more manageable steps. By setting realistic goals, entrepreneurs can reduce the risk of failure and stay motivated throughout the journey.
8. Stay Flexible
Entrepreneurship is a constantly evolving journey. Successful entrepreneurs understand the importance of staying flexible and adapting to changing circumstances. They are open to new ideas and are willing to pivot when necessary to stay ahead of the curve.
9. Learn from Feedback
Feedback is a valuable tool for entrepreneurs. Successful entrepreneurs seek out feedback from customers, mentors, and advisors and use it to refine their ideas and improve their products or services. They understand that feedback is not a personal attack, but rather an opportunity to grow and improve.
10. Take Care of Yourself
Entrepreneurship can be a stressful and demanding journey. It is important to take care of yourself both physically and mentally. Successful entrepreneurs prioritize their health and well-being and make time for self-care activities such as exercise, meditation, and spending time with loved ones. By taking care of themselves, entrepreneurs can stay energized and focused throughout their entrepreneurial journey.
11. Take Action
Successful entrepreneurs do not let fear hold them back. They take action and move forward, even when they are unsure of the outcome. They understand that taking action is the only way to achieve their goals and make their vision a reality.
12. Take Calculated Risks
While taking risks is important, successful entrepreneurs also know the importance of taking calculated risks. They carefully assess the potential risks and rewards before making a decision, and have a backup plan in case things don’t go as expected.
13. Trust Your Gut
While research is important, successful entrepreneurs also trust their gut instincts. They understand that sometimes you have to take a leap of faith and trust your intuition. Steve Jobs, the co-founder of Apple, once said, “Have the courage to follow your heart and intuition. They somehow already know what you truly want to become.”
14. Embrace Failure
Taking risks inevitably leads to failure at times. Successful entrepreneurs understand that failure is not the end, but rather an opportunity to learn and grow. They embrace failure and use it as a chance to improve and refine their ideas.
The art of risk-taking is a critical component of entrepreneurship. Successful entrepreneurs understand the importance of taking risks, doing their research, trusting their instincts, embracing failure, taking action, and surrounding themselves with supportive people.
Aspiring entrepreneurs can boost their chances of success and make their entrepreneurial aspirations a reality by adhering to these guidelines.
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