Success Advice
My Mentor And Boss Shocks Me By Quitting – How To Be An Inspirational Leader

I had a last minute meeting appear in my diary late last Wednesday titled “Team Announcement.”
Something told me that in a few hours everything was going to change. I was right.
It’s been two years now working in what I would describe as a dream team.
We’re all crazy intrapreneurs in my team and we think outside the box. We challenge each other to go even further. We disrupt the traditional business models because that’s all we know how to do.
To some we are crazy: to all of us, we want to do something meaningful.
Who is my departing mentor and boss?
In one word, “Gandhi.”
He’s a Buddhist guy with a Yoda philosophy on life. Each day he says something out there and it takes me days to figure out what he means. There is no straight answer because everything has a meaning when it comes from him. The meaning often takes a while to figure out though.
Each day, in our team at work, it’s like preparing for the ancient Japanese Battle of Sekigahara. Every day we have strategy sessions to work out how to take down our enemy. When we get dealt a major blow we know it’s only one of the many battles we face. Overall, we’re optimists led by the chief of the army – my boss and mentor.
His departing gift to me
The challenging thing for my former boss is that he loves to give gifts, yet he knows I don’t like material things. Then, one morning on the train, shortly after the announcement, I get a message on LinkedIn from him. The message read:
“…this is my gift to you.”
My foes will become nothing.
My friends will become nothing.
I, too, will become nothing.
Likewise, all will become nothing.
Just like a dream experience,
Whatever things I enjoy
Will become a memory.
Whatever has passed will not be seen again.
With those eight lines of wisdom, my life and career were set to change. He was giving me a message. He knew me better than most and he knew how much this was the best gift he could give. I then saw him at work later and he said:
“When the student is ready, the teacher will appear.”
He knew deep down that I was upset he was leaving. He knew that I wanted the dream of our team to continue with him at the reigns of the army. What he figured out I needed was the reassurance that the next chapter of my career would soon begin.
He wanted me to know that the next great leader would appear when I (the student) was ready. Just as he had come into my life when I was ready, so too would the next boss and mentor.
While having a chapter in your life and career come to a close is hard, it’s exciting at the same time. I’ve learned that uncertainty about what’s next is the beginning of the next massive opportunity. Nothing stays the same forever although I sometimes wish secretly that it would.
All you can do in these moments of your career is be grateful. The last two years have been the happiest time of my time in any business.
Here are the lessons my boss and mentor taught me:
1. Inspired people change the world
My boss never tried to tell me how to do anything. He always led every conversation with inspiration to do something great. He didn’t want us to be mediocre and be like everyone else. The fact we were a bunch of misfits and didn’t fit in was what he wanted us to embrace. He wanted us to be proud of our unique identity.
Inspirational leaders don’t focus on the how; they focus on the why. Because our team knew why we existed and what our mission was, we always found a way. When our critics laughed at us, we chose to push on. In front of our critics, we always showed respect and smiled. That smile came from a sense that the good guys would win. That good would prevail evil.
Our team was inspired to change the face of our industry. We went after the big stupid goals that everyone said to run a mile from. We put our careers on the line every day. We took calculated risks that others thought were haphazard.
“Nothing, my boss taught us, should ever be done without a why. Everything should have a purpose”
2. Relationships always trump the price paid
Many of the clients we dealt with as a team came about through relationship not price. Each of our clients have become like friends. Doing business with my boss and the team feels like going to a family BBQ. My boss taught us that doing business should be based on trust, your value proposition and the feeling of partnership. Partnerships are based on win-win scenarios.
Both sides in every business interaction should feel like they have won. That’s how you know you’re on to something. That’s the way business should be.
3. Solve real problems
My boss has a fancy job title and with that comes lots of people who want to pitch a product or service. After some meetings, where we saw something cool, my boss would look very pissed off. I’d ask him what was wrong. He says:
“Tim, what problem are they solving? If you’re not solving a problem then you shouldn’t be asking us to buy from you!”
I thought about that often and realized he was spot on. There’s a lot of clever marketing and companies that have raised money from thin air. These companies only make it when they solve a real problem.
Whatever you do in your career, do your best to try and solve a problem. The bigger the problem, the more money you’ll get for solving it.
4. Critical thinking is a rare trait
The one thing that frustrated my boss: lack of critical thinking. Day-to-day in business, we deal with many different characters. Each character forms part of solving a problem (cause that’s what business is after all).
The ability to solve problems effectively, my boss believes, is to use critical thinking. This means that you commit to the following:
– Thinking clearly before deciding on the appropriate action
– Identifying any rational biases beforehand
– Thinking about the connections between different ideas that could form a potential solution
– Being rational about your approach
It’s surprising how rare the superpower is of critical thinking. My boss taught me that it’s something to constantly aim for and to use in business wherever possible.
“Churning out the same old solutions to the same old problems will not move humankind forward. We can all change that”
5. Political capital
Throughout the last two years, it felt like we were facing into a different crisis weekly – such is life. The temptation, my boss taught me, is to try and solve every single one. The challenge with that way of thinking is best summed up through a phrase he drilled into my head like a jackhammer: “Political Capital.”
A lot of business encompasses what you would see day-to-day in politics. Each senior leader is a politician, and every politician only has a certain amount of political capital that they can spend on these weekly crises. My boss taught all of us to spend our political capital wisely.
This political capital over the last two years has been the currency we have used to buy our way into a vision for the future that some may say looked “laughable.” Massive change and seeing things before they happen often involves a lot of critics. The key I’ve learned is to turn these critics into supporters, rather than enemies. As I said before, business is very much like a strategic battle.
6. Customer focus
So many organizations have this concept of customer centricity at the forefront of what they do. It’s not always a reality though. My boss made sure that I understood the importance of making sure the customer was top of mind with every action I took.
I shouldn’t be trying to build anything without having the customer’s input every step of the way. It’s easy to say, but very hard advice to follow. I learned from my boss to do this, or face problems down the road when it’s too late to change.
7. Storytelling futurists matter
Many of our competitors over the last few years were able to win in markets where we were unable to. My boss taught me that the reason our competitors could achieve this goal was because they told better stories than us and spoke about the future.
These competitors spoke about the future and tried to play a part in it. They released products that were way ahead of their time even if they didn’t get the immediate revenue uplift.
Telling stories about the future and releasing products ahead of time gives you a reputation for being a market leader in innovation.
All of us are biased to spend our money with companies who appear to be creating the future we have always dreamt of, even if in reality they are not executing the way it’s perceived they are.
Steve Jobs saw the future of consumer electronics; all of us have the ability to see the future of our industry and play a part in that story.
Stories hold immense power to those who know how to tell them.
Stories make us take action.
Stories inspire us.
8. Your boss can be your best friend
The last two years of my life have been a rollercoaster. Multiple romantic disasters. Huge career wins like going viral all over the Internet. I’ve seen colleagues have major illnesses and even seen crowds of people die right in front of the office I work in.
Through each event, my boss has been there. Like Yoda, he’s always had some words of wisdom that don’t give me the answer but help me find it deep within myself. He’s never given up on me. He’s always inspired me. He’s believed in me and the simple idea that I – just like you – can change the world.
He’s made me see that this life is so short and so is my career.
He’s shown me that everything becomes nothing at some point.
So if everything becomes nothing, then all we have is right now.
I don’t know what the next chapter of my career looks like. I don’t know if I’ll ever have a boss, teacher, or friend like this great man ever again. All each of us has is right now. Enjoy it because change is certain.
So is the way you think about change and the awesome opportunities that come with it. It’s time for me to take a break and have a holiday.
I hope you learned a thing or two about leadership from my boss. I know I certainly did.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
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Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
-
Build diverse talent pipelines
-
Embrace flexible work models
-
Design compelling career paths
-
Simplify HR processes
-
Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
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