Archives 2025

What is worse than being a boss? Being a bridesmaid – 3 Leadership Hacks

A recent Google SEO search found that the only phrase searched for more often thanI hate being a boss’ is ‘I hate being a bridesmaid.’

My perspective on the latter is limited, but as a many-time usher and best man, I hated renting that ill-fitting, used suit.

Likely, as much as ladies hate to buy that poufy dress, they will only wear it once.

I surveyed clients to find out what they hated about being a boss:

  • 90% of new leaders felt their company failed to prepare them for the new role;
  • 42% of new managers had no idea what they needed to do to be successful;
  • 50% only took the job because it came with higher pay; and
  • 75% did not want to be responsible for people

Most organizations do a lousy job of preparing people to be promoted.

Many supervisors are thrown into the deep end to sink or swim.

They described their job as stressful and overwhelming and often regret being promoted.

If you are being considered a leader and in the absence of other supports, I would suggest you do three things:

3 Hacks to Avoid Being the bridesmaid:

 

1. Ask Your Boss For Their Performance Objectives 

Everyone has a boss – even your boss.

And everyone has been given performance objectives.

Schedule time with your boss and ask how you can support their success.

Then, take responsibility for following up to see how to work together on those objectives.

Just as you contribute to your boss’s success, your Team contributes to yours, so ensure they understand your expectations.

Click to learn about partnering with your boss.

2. Resolve Difficult Situations

You will face difficult situations.

Your people will have personal issues. Interpersonal conflict, and performance issues.

Do not let them fester

Commit to dealing with these issues promptly. 

Remember, you are not in this alone. It may feel like that was the case, so get support from your boss and the HR Team.

Click to learn about challenges

3. Schedule time with each member of your Team

Giving instructions and then walking away, hoping that everything will be done according to your expectations, is the ultimate in management irresponsibility.

Get out from behind your desk and see what is going on.

Ask them what they are, when, whether they are on a deadline, and whether they need help.

Remember that the quality of your questions and conversations will give you all the information you need to ensure you can meet your objectives.

Click to learn more about talking to your people

Finally

Do not be passive.

You are talking about your career, success, and peace of mind.

Do not wait for direction from your boss or company, which may not come promptly or at all.

Invest in yourself through coaching, mentoring, and professional development.

What is the one thing you need to turn a trusting team to a high performing team?

What is the one thing you need to turn a trusting Team into a high-performing Team?

Most people want to be part of something big!

But how do you get there?

The most amazing experiences in my life were when our work was hard and challenging. Like carrying a sledgehammer for weeks, working so hard the inside of my eyelids were sweating or flinging myself off a cliff.

People want and need to be challenged. Just think of camping when the weather was perfect, and the equipment all worked perfectly: now remember the coldest, wettest, most miserable camping trip you were ever on. I bet the most vivid memories come from the hard and challenging experience.

Work experiences are the same. Remember:

  •  When you should have failed and still succeeded;
  • When there was a critical deadline at work, and you pulled the rabbit out of your hat and met the deadline,

I bet these memories likely feel like they happened yesterday.

When a third of a town was lost to a wildfire, I led a Team that rose to unbelievable challenges and supported 15,000 evacuees. It was an experience that no one will ever forget. But none of those people will remember the hundreds of times when the day’s work just got done.

The challenge to you as a leader is how to create those opportunities. You don’t have to create a natural disaster to do it; try to:

  • Create the chance to work on projects that stretch abilities
  • Set the highest standards for yourself and watch the people who trust you strive to live up to them
  • Build a sense of healthy competition within your teams.
  • Create an environment where people show up to work every day and do the best possible work at the minimum acceptable standard standard.
  • Allow people to take courageous risks.

Embracing the Unknown: A Journey of Experimental Faith

I love this quote from Rick Rubin:

“When we sit down to work, remember the outcome is out of our control. If we are willing to take each step into the unknown with grit and determination, carrying with us all of our collected knowledge, we will ultimately get to where we’re going. The destination may not be one we’ve chosen in advance. It will likely be more interesting.”

This idea of “experimental faith” profoundly resonates with me. It’s not about unquestioning optimism or expecting miracles. It’s about trusting the process, even when the path is unclear. It’s about courageously stepping into the unknown, armed with our experience and knowledge, and allowing the journey to unfold organically.

My Journey with Experimental Faith

I’ve experienced the power of experimental faith firsthand throughout my career. In my early days as a leader, I was weeks into a project with no clear solution. It was terrifying, especially given the tight deadlines. But I noticed that the seasoned leaders and managers remained calm. They trusted that a breakthrough would emerge, and it always did.

Years later, I encountered a similar pattern when I focused on my writing. With every project, there came a point when I felt utterly lost. The blank page loomed, and the uncertainty reared its ugly head. But again, I learned to trust the process. I kept writing and exploring, and eventually, the path would reveal itself.

Read more about faith & Trust

Faith Borne Out of Practice

My friend once described faith as “making it up as nobody knows the difference anyway.”

But really faith is confidence borne from practice.” The more I practiced my craft, whether consulting or writing, the more faith I developed in myself and the process. This wasn’t ‘making it up’ or ‘blind faith’ but faith grounded in experience and the knowledge that I could rely on my skills and intuition to guide me even when things seemed uncertain.

Rick Rubin’s Wisdom

Rick Rubin echoes this sentiment in his book, The Creative Act: A Way of Being. He emphasizes that experimental faith is not about expecting miracles but honing our ability to do the work and adjust as we go. It’s about embracing the unknown, trusting our instincts, and allowing the creative process to lead us to unexpected and often more interesting destinations.

Get your Culture checklist

This philosophy has been a guiding principle throughout my career.

But I probably couldn’t have named it. So thank you, Rick Rubin, for naming what allowed me to embrace challenges, navigate uncertainty, and ultimately achieve outcomes that I never could have imagined. 

Rubin, R. (2023). The Creative Act: A Way of Being. Penguin Press.

Embracing the Unknown: Navigating Difficult Conversations

Let’s face it: Most of us don’t relish the thought of difficult conversations. They can be uncomfortable, stressful, and sometimes downright awkward. But as leaders, we can’t afford to shy away from them. They’re crucial for building trust, resolving conflict, and fostering a healthy work environment (Stone, Patton, & Heen, 2010).

What Makes a Conversation “Difficult”?

Read more about using silence in conversations

For our purposes, a difficult conversation is any situation where:

  • The stakes are high.
  • Opinions vary, and emotions might run strong.
  • Both parties need to maintain a working relationship.

Think of those times when you must address a sensitive issue with your supervisor, a colleague, or a Team member. These are the moments that call for a thoughtful and strategic approach.

Four Steps to Navigate Difficult Conversations

I’ve found a simple four-step framework to be incredibly helpful in navigating these situations:

  1. Preparation: This is where the real work happens. Before jumping into the conversation, take some time to reflect on your intentions. Ask yourself:

  • What do I hope to achieve?
  • What outcome do I want for myself, the other person, and our relationship?
  • What are the facts of the situation, and how might a neutral observer view them?
  • What does a successful resolution look like?
  1. Initiation: Set the stage for a productive conversation. Choose an appropriate time and place, and be mindful of your tone and body language. Start by acknowledging the difficulty of the conversation and expressing your desire for a positive outcome.

  2. Discussion: This is where active listening and clear communication are essential. Be sure to:

  • Focus on the issue at hand, not personalities.
  • Use “I” statements to express your perspective.
  • Ask clarifying questions to ensure understanding.
  • Acknowledge the other person’s perspective and emotions.
  1. Conclusion: Summarize the key points discussed and any agreements reached. If necessary, schedule a follow-up conversation to revisit the issue.

Read about not Eff’ing up conversations

Additional Tips for Success

  • Be kind but truthful: Honesty is crucial, but consistently deliver your message with empathy and respect.
  • Ask “dumb” questions: Don’t be afraid to ask seemingly obvious questions. They can often reveal hidden assumptions and lead to deeper understanding.
  • Offer “dumb” suggestions: Brainstorm freely, even if some ideas seem outlandish. You never know where creative solutions might come from.
  • Be willing to do the dirty work: Don’t shy away from tackling the challenging issues head-on.
  • Have the other person’s back: Show them you’re on their side and committed to finding a mutually beneficial solution.

Remember: Difficult conversations are an inevitable part of leadership. By embracing these challenges and approaching them with a thoughtful and strategic mindset, you can transform them into opportunities for growth, development, and stronger relationships.

References: Stone, D., Patton, B., & Heen, S. (2010). Difficult conversations: How to discuss what matters most. Penguin Books.

How Do You Want People to View Your Advice?

Advice.

As leaders, we give quite a bit of it—so much that we probably don’t think that much about it. We need to think much more about it. We need to consider it in three dimensions: why we are delivering it, how we are delivering it, and what we want people to do with it.

Let’s look at each dimension.

Why Are You Giving Advice?

I believe that whether we are thinking about it or not, every time we give advice to anyone (as a leader, parent, spouse, friend, or stranger), we are considering that advice somewhere on the scale between taking it as gospel (do it exactly like this) and its guidance (here’s something to consider). But these two goals aren’t exact or perfect – instead, we see our advice somewhere on this scale:

In my experience, most leaders consistently place their goal for advice on this continuum, whether based on habit or style or without even thinking.

We call the tension between the ends, both/and thinking, the underpinning of being a flexible leader.

There are times when the context warrants your goal being far to the “gospel” left (when the context is clear and the outcomes and situation are known), and times when perhaps there are many unknowns and your experience might be helpful but should be seen on the “guidance” right side of the scale. Even given those considerations, you might have goals for delegating and developing your Team members, leading you to lean to the right or left on this continuum.

First, I would suggest that you be clear about your intention—why are you giving this advice, and how do you want others to use it? If you don’t think about that, how people interpret your advice will be left to their perception, which might not match your goals or needs.

What Do You Want Them to Do with It?

Your answer to this question flows from your intention. Consider this situation and these two employees. You face an apparent problem. You have seen this situation or challenge before and have successfully overcome it with a specific set of reliable steps.

One has been on your Team for a couple of months. He shows promise but lacks extensive experience and doesn’t know all the players involved in the situation well.

The other has been on your Team longer. She does have experience with this situation. She also shows great promise and is ready for advancement and skill development.

I propose that each employee has different contexts, so your intentions for each differ. Based on this information, even though you have a proven process each could follow, you should have slightly different goals for each.

I might lean the intention of my advice to the left for less experienced – giving him more of a “how to” approach and more to the right for the other – giving her guidance and things to consider.

Note that your current intention concerns your experience and knowledge and how you want others to apply it.

Hopefully, it will be in a way that makes either Joel or Jael crystal clear on your expectations.

How are You Delivering it?

The big idea is that your delivery should match your intention and desired action.

Given your positional power, if you want people to follow your advice verbatim, deliver it clearly and maybe even pointedly. If you have a current approach and want them to follow it, clarify it.

But if you want your advice to be seen as guidance – and more suggestion than imperative – make sure that is clear, too. You will likely want to use a softer tone and delivery as well.

As “the boss,” people may likely default to a “yes, boss” belief about your intent unless you are clear about yourself and with them.

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I really appreciate being constantly reminded of my mistakes! 8 ways to deal with people issues.

I have made a lot of mistakes.

Some of them were pretty spectacular. While formal training, my master’s degree, and supplementary reading have taught me the theory of leadership, my mistakes have taught me more than I care to admit.

My first leadership lesson happened when I was barely six or seven years old. I was a voracious reader, devouring comics, magazines, superhero books, and war stories. The best of all were the Hardy Boys books. I wanted to read every single Hardy Boys story. One day, I went into the drugstore in our small farming village and spotted a Hardy Boys book I didn’t own. I didn’t have the money for it, so I slipped it under my shirt and walked out. On the surface, it was a small act—but however you slice it, it was stealing. 

 

When I got home, of course, I got caught. A shiny new hardcover book couldn’t just appear in our house without everyone knowing about it. I was taken back to the drugstore to confess to the store owner. My dad waited outside while I went in. I made my way to the rack of books, returned the stolen book to its rightful place, and left. Dad asked if I had spoken to the owner. Keeping my backside in mind, I told him the truth. 

 

I was turned around on the spot and, once again, escorted back into the store to “face the music.” I admitted my wrongdoing and apologized. To my surprise, the store owner only scolded me gently. More importantly, he thanked me for owning up, returning the book, apologizing, and acting “like an adult.” 

 

The trip back home felt like my own green mile. I was sure I was heading to the gallows, but it was over—my dad left it at that. Looking back now, I cannot recall ever hearing about the incident again. 

 

The lesson I learned from that ordeal was this: when something is over and dealt with, it’s done.

Managing Issues Effectively

As a leader, your most frequent challenge will be managing the issues that inevitably arise when dealing with people. Try to remember—and consistently encourage others—to cooperate. Ultimately, your value as a leader will be judged by the performance of the people who make up your Team. And their performance will reflect your total personality, attitude toward life, and particularly your approach to people. Your success or failure will be a direct result of how well you align your organization’s goals with the career goals of your people and deal with any friction caused by misalignment.

The following suggestions will help you achieve results:

  1. Focus your attention chiefly on results rather than the activities you think will get you there. Everything should be about results.
  1. Plan and organize effectively.
  1. Communicate objectives properly, with time targets, established measurement systems, and designated accountability.
  1. Establish performance expectations so all concerned will be focused and will know how their performance will be measured.
  1. Communicate a “results-oriented” attitude to encourage people to develop self-reliance and confidently achieve their goals.
  1. Motivate people to their peak achievement.
  1. Be creative and help others develop their creative potential.
  1. Track all progress so that what is planned is achieved.

Get eight suggestions to improve how you motivate

How Do You Measure Up When It Comes to Issues Management?

Read each statement or question below.

On a scale of 1 to 5, with 1 meaning “never” and 5 meaning “always,” mark an “X” where you think you are today.

Then, mark an “O” where you would like to be.

Consider the above article and commit to one thing you can do to improve your score.

1.     You look for the critical factor(s) that must be changed before anything else can be changed or acted upon to unearth the real problem.

1                        2                      3                      4                     5

2.     You make sure that your problem-solving objectives reflect the organization’s objectives.

1                        2                      3                      4                     5

3.     You consult all who should be consulted before making a decision.

1                        2                      3                      4                     5

4.     You evaluate your decisions by predetermining their possible impact on people and things.

1                       2                      3                      4                     5

5.     You predetermine how long the organization is committed to your decisions.

1                        2                      3                      4                    5

6.     You ensure your decisions do not violate established rules, policies, procedures, good ethics, or morality.

1                        2                      3                      4                    5

7.     After defining and analyzing problems, you develop as many alternative solutions as possible to widen the range of choices before coming to a final decision.

1                        2                      3                      4                    5

8.     You are skilful at timing. You determine whether or not the situation is something urgent requiring quick action or whether long, consistent effort is needed.

1                        2                      3                      4                    5

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