Leadership Challenge: Leading the More Experienced

Leadership challenge: You have been hired to lead a team older and more experienced than yourself. Some of them seem determined to break you. Some seem indifferent. Some seem to treat you like a kid.

A common challenge that young managers face is managing older employees. The problem usually presents itself in the form of egoistic defiance of authority. The same situation may arise when a new employee is promoted to a position of leadership over more experienced employees, irrespective of age differences.

The new manager would respond in one of three ways:

  • Let them be. Often letting the difficult team member do whatever they please to avoid confrontation seems like the easy way out. Even though this might seem to work in the beginning, existing problems and friction will escalate until someone quits.
  • Show them who’s boss. It is not unnatural for young managers to feel insecure or threatened by difficult team members. One way to fight it is by exercising authority even to the extent of exploiting it.
  • Lead the team. Despite the challenges a manager faces, good leadership has the power to win over the most difficult employees. It’s how you lead that makes a difference in the way your team follows.Leading older2

You can make this leadership transition smoother for both youself and your team.

Be competent. It’s not the same as being perfect but being a leader should demand the best out of you and your team. It doesn’t mean that you need to know everything but it sure means that you are not afraid to be a coach and a leader to the ones who know more than you do. Don’t hesitate to display your strengths.

Trust and respect your team. Get over your doubts- no one is trying to tear you apart. Partner with your team and respect them even when you have to be firm. Maximize your team’s expertise and years of experience. Delegate effectively without giving in to favoritism.

Be a coach. The reason you are the manager and your team member is not is because you are trusted to coach your team to bring change. Challenge routines when there are better alternatives and include your team in the process. People are more vested in the changes that they can contribute to.

Manage the relationship. It is your responsibility as the leader to take the first steps in managing your relationship with the team. Being proactive in managing any existing tension will help you emerge as the leader. Different members of your team will need to be managed differently and the sooner you figure that out, the easier your transition will be.

Keep your manager in the loop. Discuss your strategies and seek help when needed.

Remember that leadership is challenging. Even the best leaders are criticized for trivial reasons. Be persistent. You will figure it out.




Leader, are you a visionary?

One of the many advantages of leading a small company is the amount of direct influence one can have on the company’s culture. You can also have more control over every hiring decision, every amount spent and every operational detail. But if you own a small company, you know how all these influences and control points can add up to choke your ability to be the company’s visionary and simply turn you into a glorified operations manager.

Irrespective of the size of your company, one of your main responsibilities as a leader remains the same – set a clear vision of the company for your employees to follow. The success of your company and your team depends on it. With a clear understanding of what the company stands for and where it’s meant to head, your team will be more successful and so can your company. Without a clear understanding of the vision, your company will end up spending resources where it is not necessary and accelerate failures.

Maybe you will have to share the vision with your team only once, but in most cases, you will need to remind them often with words and by example. Do it until they make it their own and continue even beyond that.

Mid-year is a great time to take a step back and review your success as the company’s visionary. Do you have a clear understanding of your company’s vision? When was the last time you reminded your team about it? Does your current team exemplify your company’s vision and reflect your company’s brand when working with each other and with customers? What changes are necessary for the rest of the year?

Be the leader who your team chooses to follow. Be the visionary. Then passionately lead it into reality.

I quit working 9-5.

Every entrepreneur that I have spoken to has endorsed this truth: Starting a new business can be both exciting and overwhelmingly exhausting. Most entrepreneurs start their own ventures because they are tired of the routine 9 – 5 work schedule but end up working longer hours when pursuing their dreams – which is a extremely impressive!

Even when entrepreneurs are not working, they end up thinking about work. Entrepreneurs insomnia is the inability to rest from work at night. It’s hard to detach from work because the lines between work and passion cease to exist. Be reminded that at the end of the day, it is work and unless an entrepreneur takes time to recover, burn out and lack of motivation will be hard to kick aside. Here are five solid tips to help you remain motivated in this entrepreneurial journey.

  • Separation between work and rest is important for entrepreneurs. Taking a break from your work can help you become more productive and creative. It is when it gets a chance to rest that our brain often creates wonders. Find out what helps you rest and recover and be intentionally consistent about incorporating it into your schedule.


  • Engage with your customers and supporters, not just to grow your business but also to get affirmative feedback. Affirmation can be a strong motivator and can relieve negative stress. Entrepreneurs often ignore current supporters because they are too busy pursuing new ones. Keep both friends and enemies close – both groups can motivate.


  • Pursue hobbies. Just because you started your own company does not mean you must sacrifice all your other interests. Starting your company will most likely be all work for the first phase and there might be days when you will question your entrepreneurial journey. Hobbies can encourage innovation.


  • Keep improving your skills and strategies. Make use of every opportunity to learn something new. Your company will continue improving with you.


  • Enjoy the work an celebrate successes because when you enjoy what you do, failures will truly turn into stepping stones for greater success. As Drucker said, “Failure should always be considered a symptom of an innovative opportunity, and taken seriously as such.”


As an entrepreneur, what are some tips you wish you had heard before you started? Write to theoverseasmagazine@gmail.com. 

Team Issues? Sprinkle a dose of Care!

Employee engagement is directly proportional to how appreciated your employees feel. By ‘feel’ I am not referring to their emotions alone. No matter what personality types you have on your team, here are five simple ways to improve your team’s engagement and performance.

Value their time. No matter how cool a boss you may be, your team can remain disengaged if you waste their time and effort. Inefficient projects, inadequate planning and failure to implement ideas effectively result in lack of motivation. This requires a manager to put in thought when designing team objectives and projects. It is also better to provide some free time to your team when there’s nothing pressing to do instead of constantly keeping them busy just because ‘they’re getting paid for it’. If you don’t value your team’s time, they will not value yours or the company’s.

Provide effective feedback. What’s worse than no feedback? Ineffective or delayed feedback. Providing feedback on your team’s performance shows that you’re paying attention. Affirmative feedback and constructive feedback – both work as long as you discern the timing well.

Related: Effective Constructive Feedback

Encourage leave days and breaks. Have you heard of companies that grant unlimited leave days to their employee? It works for them because it improves employee efficiency in a lot of ways. Employees work harder and don’t mind long hours because they know that they can take a break from work when they need to. Therefore, it works in favor of both employers and employees. Even if you’re the boss of the smallest team in the company and cannot change assigned leave days, you can find ways to help your team maximize breaks and leaves without breaking rules. It will be rewarding.

Treat them to a meal. Food and especially the good free kind is one of the easiest ways to show your team that you care.

Stand up for them. Your decisions affect your team. Leaders are respected because they protect their teams and help them succeed. Recommend your team for capacity building initiatives and promotions. Help them get those incentives and bonuses. Leaders who simply pursue their own agenda break their teams up and fast track the company towards failure.

Employees are your BIGGEST assets. Treat them royally.


Are you a ‘slasher’?

“Have you been doing too much?” Most of the people I have spoken to in the last few weeks have described their weeks as being very busy and themselves as being very tired. Whether it’s multiple jobs or multiple projects, supporting the family or being a student – there are times when we realize that we are doing too much… and sometimes with little to show for it. It helps to remember the big picture especially when you are busy.

When I first read about the concept of Project Portfolio Matrix (PPM), I did not connect it to anything beyond work projects. Basically PPM helps to prioritize projects in alignment with goals while maximizing the use of available resources. In other words, it helps to maintain an overview while handling multiple projects. The matrix can be used to evaluate multiple scenarios and could prove very useful when applied correctly.

The idea of applying the matrix to both work and private projects was suggested in The Decision Book. The chapter on PPM was dedicated to ‘slashers’ – people who cannot give a single answer to the question, ‘and what do you do for a living?‘. Reminds me of people who feel the need to constantly juggle multiple projects, even when they don’t need to. And more often than not, they fail to keep it all perfectly balanced, dropping key projects because they lack the necessary overview. In the end no real progress is made.

In the chapter, the author was particularly talking about the matrix in relation to ‘objectives achieved’ and the ‘amount learned’. Give it a try: You can use the parameters that are relevant to your situation. Costs can be considered not only in terms of money but also resources such as friends, energy, stress levels. The author suggested using the x-axis as the measure to determine how a project is helping you achieve your overriding objective. On the y-axis, you can then plot how much you are able to learn from the project.

The author suggested ways to interpret the results and I will quote it directly from the book:

  • Reject projects if there is nothing you can learn from them and if they do not correspond to your overriding vision.

  • Projects that you can learn from but do not correspond to your vision are interesting but will not help you achieve your objective. Try to change the project so that it serves your vision.

  • If a project corresponds to your vision, but you are learning nothing new, look for somebody else to do it for you.

  • If you are learning something and achieving your vision, you have hit the jackpot.

If you were using this tool in an area like fundraising, it could mean plotting your fundraising target on the x-axis and plotting your strategic efforts on the y-axis. Then you could measure how strategic your efforts really are in achieving your goal and invest time accordingly. Sounds like a winning strategy.

Maybe we will end up as permanent ‘slashers’. We can make all that busyness count towards our overriding vision.


Quotes from: The Decision Book by Krogerus and Tschaeppeler.