Category: Achievement

Challenging Assignments for High Performing Employees

Challenging Assignments for High Performing Employees

Last week, one of my coaching clients asked, “How can I continually challenge my high performing employees?” It’s an important question. Interesting and challenging work motivates our employees to put in extra effort, learn new skills, and decreased the likelihood that they will leave our organization.

Business People Meeting Conference Discussion Working Concept

For work to be challenging, it must meet the following three requirements.

Three Requirements of challenging work:

  1. The work requires the employee to develop and use a new skill set. For instance, I had a manufacturer production manager who excelled at his job, instead of letting him become stale, I assigned him the task of training the sales managers on the manufacturing process. It was a stretch assignment where he learned facilitation skills while using his knowledge of the manufacturing process.
  2. The work is a step to a higher purpose. The work should connect to the employee’s career or personal goals. I had an employee who wanted to move into a managerial position, so I asked her to lead a small project for the department. During the project, she had the chance to prove to me that she had the necessary leadership skills to become a manager. It also gave me an opportunity to mentor her on where she could become a more effective leader.
  3. The work should have a risk of failure built into it. The employee should feel that if they do not succeed, there would be a negative consequence on their career. This external pressure increases the employee to focus on the challenge at hand. I was once asked to develop and present our department’s twenty-six million dollar budget to the chief financial officer. I knew if I did not do my job well, I would impact our department for the next fiscal year and probably hurt my standing within the organization.

Note of caution: What may be challenging for one employee might be overwhelming to another or might be trivial to another. It is essential we know our employee’s performance level and what will motivate them and what won’t. The goal of providing an employee with a challenging assignment is to improve their value to the organization.

Ways to challenge employees:

  • Require the employee to learn something new. This act puts the employee in the role of the novice, asking them to start anew, focus on the foundational information that will challenge them to more significant insights about their present level of performance. In the process of learning something new, our brain triggers changes in neural pathways, providing us different ways to look at old problems.
  • Change the parameters of their job: What is easy to complete in one hour is much more challenging to achieve in thirty minutes. Shift parameters such as time, budget, supplies, number of clients, etc. to challenge the employee to work at a higher level. In working with one company, the general manager and I continued to add responsibilities to the team until the job was increasingly challenging. We finally stopped when we notice a reduction in overall performance.
  • Push the employee out of their comfort zone: All of us love living in our comfort zone, it is where we are secure, psychologically safe, and most confident, but we are not challenged. By asking an employee to step outside of their comfort zone by doing a new responsibility, working with a new team, or giving them a stretch assignment, challenges them to improve their performance.
  • Involve the employee in higher-level decision making. Asking the employee to think at a higher level, requires them to change their perspective challenging assumption they may have. For instance, I had a supervisor whom I knew was ready for more responsibilities, so I ask him to manage the department’s accounts. This task not only required him to learn new skills, but he also challenged him to work at a higher level of decision making.
  • Have them mentor another employee: Working with another employee to help improve their performance can be challenging to our high performing employee because they will need to use different influencing skills to help the other employee be successful.
  • Ask them to change behavior. One of the most challenging things we can do in life is to change one of our behaviors. Unfortunately, all of us have behaviors or habits that are holding us back from being successful. The best approach to this is to use Marshall Goldsmith’s Stakeholder Center Coaching process where the individual’s stakeholders help the employee identify one behavior if changed would positively impact the employee’s performance. Then working with the employee, the manager can develop a plan to change the behavior. For most us, this will be the hardest thing we do in our career.

Motivation is necessary for an employee to reach a higher level of performance. Based on my twenty-five years plus managing employees, challenging assignments are one of the most effective ways to help high-performing employees continue to be motivated. Challenging projects tap into an employee’s intrinsic motivation; where they ask themselves to perform at a higher level.  

Before Challenging the Employee Questions to Ask Yourself?

  1. Is the employee ready to take on an additional challenge at work? Is their performance strong enough that would allow them to take on additional responsibility?
  2. Is the employee motivated to take their performance to the next level? Alternatively, in other words, what reason does the employee want to perform at a higher level? What we have found is that those employees who have a high level of intrinsic motivation will be the drivers of their organization and will want to improve. Extrinsic motivation is a short term fix but will not keep employees performing at a high level.
  3. What knowledge, skills, abilities, or experience do they need to have to advance their career? (Career advancement should not always be about moving up in the hierarchy of the organization but giving them opportunities to try new things, oversee different areas, and of course get prepared where they can make more money.)
  4. What task, responsibility, project, or assignment will stretch them while at the same time, not hurt the organization too bad if they fail?
  5. What support can you offer, so they are prepared for this challenging time? Are there classes/seminars you can send them to? Is there knowledge you can share? Is there a mentor in the organization that would help them be better employees?
  6. Can you build milestones/path for them to get ready to take on a much bigger responsibility?
Most Expensive Lunch Ever

Most Expensive Lunch Ever

This week someone paid $3,300,100.00 to have lunch with Warren Buffett.

Now that is an expensive lunch.

It was for a charity auction, in fact, it is the 19th time Warren Buffett has auctioned off lunch.

It got me to thinking about what questions I would ask Mr. Buffett. Figuring, this is your typical business lunch, I would have approximately ninety minutes to learn as much as possible from the Oracle of Omaha.

Most of us will never get the chance to have lunch with Warren Buffet. However, we will all have an opportunity to meet with people who could influence our careers and our lives. Every month, I talk with individuals who are looking for advice in their careers, or their leadership skills.

I hate it when people ask stupid questions, like how long have you been working at True Star Leadership? It means that they haven’t taken time to check my LinkedIn Profile or website ( Maybe it’s not stupid, just lazy.

For us to use the time wisely, we need to have a plan. Here are six things we should always do no matter whom we are meeting.

  • Decide on Your Goal: What information or help do you need from this person to help you move closer to your goal? What is their expertise or area of interest that you want to utilize?
  • Do your research: Learn more about the person you are meeting. Even if you just do a review of their LinkedIn Profile, at least get to know them. If they have a book, blog post, interview or website, check it out. The better you know them, the better questions you can ask.
  • Be Prepared with Questions: Based on your goal and what you know about your subject, prepare some questions to start the conversational ball rolling. For instance, I once had the opportunity to meet Marshall Goldsmith, because I knew he had accumulated millions of airplane reward miles, I asked him his advice on how to make the best use of plane time. This lead to a conversation about time management and its benefits.
  • Listen More: If you talk a lot, you will miss hearing the wisdom of the person who you are meeting and will not move any closer to your goal. Let them speak and carefully guide the conversation, so you get what you need.
  • Act: In your meeting, most likely you will get advice or useful information that will help you be more successful. Take thirty minutes after the meeting to put the advice into action, even if it is just making a note to yourself about what you need to do the next day.
  • Thank them. When you leave, thank the individual with whom you met. When you get home, send a handwritten thank-you note expressing your gratitude.


If I were paying almost $37,000 per minute to talk to anyone, I would want to get my money’s worth. Even if I am buying coffee for someone, I want to make sure I am using my time and their time wisely.

Good Luck Networking,


PS: I am always open to good conversation – click here to schedule time with me.

Lessons from the Big Swim

Lessons from the Big Swim

The rain fell from the silver-grey sky onto the group of us. Standing on the windswept beach, we listened to the words we did not want to hear. The Big Swim was canceled due to the weather conditions. My brother and forty-five other swimmers had spent the better half of the year training to swim the 17 kilometers (10 miles) across the North Cumberland Strait from New Brunswick to Prince Edward Island only to be disappointed.

The lead organizer had talked about the difference between our expectations and reality and defined it as the feeling of disappointment.  On that Sunday Morning, there were many disappointed people on the beach, some cried, some sighed, some bent their head in quiet prayer. A few optimistic souls shouted, “next year,” a rallying cry to know the effort, discipline and sacrifice had meant something.

As a support kayaker and a witness to the hard-work it takes to prepare for such a quest, I too was disappointed, for me, for my brother and for all those you had worked hard to be left standing in the rain on the beach; our goal was just out of reach across 17 kilometers of turmoil and lighting.

On my way home, I could not help but think that there were lessons to be learned from the Big Swim about how to achieve our own dreams. Below are the six lessons I learned and how they can help us achieve our goals faster.

  1. Preparation: The North Cumberland Straight, 17 kilometers wide at its narrowest, is known for its strong tidal currents and roaring winds. It is not a place to take for granted. Preparation is critical to the success of any who plan to swim across it. Training started with rising early every day and swimming. First in the pool, then in a lake, and then in the ocean until the swimmer was physically and mentally prepared to make the attempt.
  2. Support: The bigger your goal, the more support you will need. The support will come in a variety of sizes, from the little to the large. Before the event, my brother’s wife gave him support to train by watching their two young kids every Saturday morning. The organizers provided constant communication to make sure the swimmers had everything they needed to be successful. The day of the event, hundreds of supporters from kayak carriers, check-in volunteers, boat captains, and family members made sure the swimmers had everything they needed to be successful.
  3. Community: Community is essential to success. My brother met and trained with a group of like-minded swimmers from his home town. He learned from their experience; shared his expertise and leaned on them as the training took its toll. In the early Sunday morning dawn, together they lessened the disappointment of not swimming with laughter and hugs, sharing the loss to diminish its impact.
  4. Limitations: We all have limitations. We can choose to let them define us, or we can push against them. In the group of swimmers who were attempting the Big Swim, the ages ranged from 11 to 73 years. None of them let their limitations define them. The eleven-year-old could have let those who said it was too dangerous for her to stop her from doing what she wanted. She did not; she was in wave three – the elite swimmers; ready to go.
  5. Drive: The swimmers who had completed the swim before said that there is a time in the middle of the straight when exhaustion has crept into your muscles, and the sky and ocean have blended into one, you think about quitting but you continue till your feet hit the sand. No matter the goal, we have all reached that place where we want to stop. Those that are successful keep going pushing forward by an inner drive toward their goal.
  6. Celebration: Soon after the announcement of the cancellation of the Big Swim, a quiet applause rose from the crowd on the beach and slowly turned into a standing ovation for the swimmers. The applause was recognizing the effort they had made to reach this point on the beach, the hard-work, the dedication, and scarifies they made. We too need to recognize our progress and celebrate our wins.


Goals are just dreams without wings.


Even in disappointment, there are lessons to be learned. Thomas Eidson once said, “I have not failed 10,000 times, I’ve successfully found 10,000 ways that will not work.” No matter what we dream of accomplishing, we can not do it without a lot of hard-work, dedication, and sacrifice. As you plan your next business adventure, think about these six lessons and how you can apply them to achieving your dreams. As a leadership guide, I help people plan their dreams and provide the necessary skills and tools for them to be successful. If you are ready to start your journey, let’s get together and begin the work required for you to reach your dreams.