Prepare Your Successor Today

Prepare Your Successor Today

Whether you have a business or you are looking to forward your personal career, it pays to have a plan in place. Finding your replacement before it’s needed is essential in order to keep continuity in the business and work, but it also requires you to let go of some ego and even perhaps overcome some fear and trust issues. 

A Harris poll found that 60% of small business owners had no succession plan in place. I study by Wilmington Trust further affirms the data, finding 58% of small business owners with no succession plans. The gap isn’t just a challenge for small businesses, many national and global organizations lack a true plan for leadership succession. 

Capabilities of today vs needs for the future

The saying, “What got you here, won’t get you where you want to go,” is certainly true when it comes to succession planning.  Just because someone is very productive and efficient at the role that is currently in, doesn’t automatically mean that they will be great at the next level. 

As you look for that next leader on your team, think about the skills that they currently have against the ones that they will need in order to be successful. Each time a person crosses a threshold from one level of leadership to another, it requires them to reconfigure their skills in order to have continued success. 

Think about a phenomenal individual contributor. They may be incredible at what they do, but they’ll need to let go of certain passion projects/tasks and learn to delegate and prioritize their time differently in order to be a leader. As they progress in their career to lead other leaders, they’ll need to change again in what they focus on, how they communicate, and spend their personal time. 

Identify and spend time with your future leader to prepare for those key skills and changes in behavior before the opportunity arises. 

Test it and realistically access

Once you figure out those key skills and attributes to develop the person around you, it’s good to test out their learnings. Here are a few ways that you can test their growth and readiness:

  • Run hypotheticals: Present real-world scenarios and talk through how they would go about navigating the challenge. You can add a sense of urgency by condensing timelines, and/or temporarily taking away resources to understand how they adapt to the environment. Give the person meaningful feedback after they complete the scenario. This is a great safe way to role-play unique and challenging parts of the role with someone. 

  • Extend some authority: There’s very little that someone do that can’t be ultimately fixed. Extend some authority to the person, so that they can get an understanding of responsibility, try it on, and provide others with a glimpse of what the person is capable of. Start small in scale, time, and impact level and add on as the person shows more comfortability and delivers on the result. 

  • Give them exposure to other parts of the business: Often when a person moves up, it means that they will be interfacing with a new area of the business. Perhaps they would take on more financial responsibility or perhaps take in a whole new segment of the business. Give them opportunities to explore those new areas early, so that they have comfortability and knowledge around them as they grow their business acumen. 

As you add in these scenarios and situations to prepare them for the next level, give them real and honest feedback along the way. It serves them and your people better when aren’t afraid to shy away from difficult conversations and coaching moments. 

During the development phase, you and the other person may realize that they are currently in their sweet spot in the career, and promoting them would do both the person involved and the team a disservice. Rest assured that learning this information, doesn’t mean that you’ve wasted effort. Quite the contrary! You’ve saved an employee from going into a job that they wouldn’t enjoy and you have saved time and money spent in replacing one or both roles. Through the process, you’ve also increased the knowledge and experience of the person that will serve them well in the role that they are currently in. 

Run the two-up exercise on yourself

Now that you’ve got some idea of succession development with your people, it’s time to put your strategy to the test to see how well you have future-proofed your key positions.  

Run the succession exercise with yourself or your leader(s): The exercise is simple enough, you simply start at the top of the team and ask the hypothetical, “This is now gone, who’s next?” You then work your way down your proverbial organizational ladder from there to check where your opportunities are. It’s not uncommon to have segments that are well-prepared for and others that are in obvious need of attention. 

Once you have built in a good layer of succession and development on your ladder take the exercise to the next level by going two-deep on the roles that you are planning succession around.  We’ve seen on countless occasions where this has real-world implications and payoff. Have you ever seen a leader leave and then the 2nd in command leave not long afterward? It happens! Going two deep on succession provides you with a natural level of protection when two drop (or promote) within a small timeframe. 

Embrace your succession planning efforts to take your team’s development and your own potential to the next level. 

Make a better tomorrow. 

Can you Turn into a Bad Boss?

Can you Turn into a Bad Boss?

“Great people are hard to find.” It’s a statement you hear a lot with hiring managers and talent acquisition friends. We had a listener question that flipped the dynamic by talking about how hard it was to find a great boss while asking the question, “Is it possible for a good person to turn into a bad boss?”

The answer is that even great leaders can find themselves becoming a bad boss if they aren’t mindful of it. While I think there are a number of reasons why people end up at this point, from being promoted too soon, to not being equipped to handle the soft skills of leadership, or personal disengagement, very few people start out with the intention of being a bad boss to others. 

So how do people get to this point?

It’s often a subtle and long journey, and the person can miss that they’ve strayed off of the right path. Here are some things to look for to help determine if you becoming a bad leader. 

Signs that you may be a bad leader

Are people bailing on you? The Great Resignation aside, have you been seeing an uptick in people leaving the organization lately? It’s said that people quit bosses, not companies and that is largely correct. While the counterargument is that it is all about money does hold some weight, especially for entry-level jobs, it becomes less of a factor for higher levels in the organization. 

If you have people leaving, especially abruptly, it likely means that they have hit their breaking point and have given up on their role. This is a strong indicator that your leadership is at play in their decision to seek employment elsewhere. 

How comfortable are people around you? We’ve all been there. It’s the feeling of having to walk on eggshells because you don’t know what will set the other person off. That feeling and dynamic can cause you to have anxiety or feel fearful to be truthful with the other person. 

How are people acting when they are around you? Are they timid to share any constructive criticism or questions about directions or a project? If so you may have a toxic environment at play where the team feels like it has to hide in the shadows in order to survive the day. If you are unsure about the hesitation of your team to share honestly, throw out a really bad idea and see what their reaction is. If there is no hesitation or pushback, you may have a team that fears giving their honest opinion. 

Who carries the trophy? When it comes to the success of your team, who is the one that is recognized for their accomplishments? Do you find yourself holding the proverbial trophy after the team wins and taking credit for all of the success? It’s an easy trap to fall into. We discussed the ego trap in the 7 deadly sins of leadership with Jennifer Thornton (EP 257

Employees can quickly see when you make the direction about yourself and can feel unappreciated as a result. it doesn’t always have to be at the big milestones wins either; are you the speaker for the group when it comes time to present to the senior leaders or clients? Are you the face of the job when all the others are the ones that did the hard work? 

Recognize how much of the spotlight you take in both the big and small parts of your and your team’s work. 

Tips to get back on track

Maybe you see yourself in a bit of the examples above. Know that hope is not lost. Just as you had a journey or experiences that led you to where you are today, you can also take a journey back to great leadership that includes and engages others in a meaningful way. 

Take the “No More” approach. We’ve talked before about the no-more approach before. It’s the idea that as you reflect back on past bad experiences that you’ve had with other bosses or companies that you commit to people under your leadership will never have that bad experience again. It’s a great way to make the best of bad leadership situations. 

Are there things that you are doing or ways that you are currently leading that need a “No More” correction? If so, commit to it and begin righting the experience of others immediately. These are often behavioral on your part so they take little discussion or debate with others to implement. 

Commit to an encouraging word a day. For most people, it takes being intentional in order to lift people up and encourage them. Try starting small by recognizing and encouraging one person a day. If you need some ideas on ways you can encourage others you can check out:

Acknowledge what others know. Your people know when you are a bad boss. instead of hiding behind new initiatives and commitments, own up to your growth opportunities and explain to them your commitment to do better. This will show them that you have an authentic desire to change, and it will keep you accountable to take the steps necessary to head in the right direction. 

It’s never too late to turn around your leadership reputation no matter how far you’ve strayed. With time, commitment, and a humble attitude you can bounce back to your former glory. 

Make a better tomorrow. 

4 Mistakes that Impact Your Likability

4 Mistakes that Impact Your Likability

Everyone wants to be liked and validated by others in some form or fashion. From a young leader all the way to a tenured executive, our actions and behaviors can be driven by the desire to be liked. 

In our quest for validation, we can sometimes make some common mistakes that work against us. Here are 4 common mistakes that impact your liability and how you can address them for your personal success. 

#1 You talk too much

Talking and listening can be an internal push and pull for people as they navigate conversations with others. People love to talk and share about themselves and a quick way to be more likable is to listen much more than you talk when you connect with others. 

That intentionality in listening can create tension in the brain. It’s simultaneously focusing energy on paying attention while also alerting you to spots in the conversation to add your story, perspective, or other items to the conversation. 

When you let the balance between listening and talking tip far into simply talking, you can quickly become less likable with others. They may see you as self-focused, uncaring, or not receptive to feedback. 

#2 You ask too many questions

“Why?” It’s the question that nearly every parent of an over-curious child tires of hearing. There is a reason why the root-cause exercise is called the “5 Whys Technique” and not the 30 Whys Technique. 

Asking questions and showing general interest in another person is great. It’s one of the secrets that we recommend to help make you more approachable and likable with others. Just like anything else in life, you can take the questioning too far and wear out your welcome in a hurry. 

I’ve known several well-intentioned people over the years that have sabotaged themselves to various degrees by asking too many questions. Think back to the parent and child example; The parent is usually happy and even excited to engage with a little one when they ask a question in order to learn. It’s the continued line of questions that ends up getting the best of a parent and causes them to lose their composure. 

Be aware of how much you are questioning others. If you see their engagement drop off as you further seek to understand, know that it is a sign to wrap it up. Continuing to ask questions further lowers your chance to get an authentic answer and adds to the impression that a person has about you. 

#3 Weak storytelling

There is power in a good story. (EP 124) If you’ve ever been to a conference or religious service, you have a higher likelihood of remembering a personal story that they told instead of all three points that they presented at the time. 

Storytelling that is not compelling serves the interest of the teller more than the audience or is overly canned can turn your audience off. 

The story is not good: A good story should be one that the person can relate to on a personal level, short enough that they could tell it to someone else, and include something memorable enough that they could recall it a day later. Hone your stories and try them out with people you trust to figure out if it’s good enough or if it should be tweaked or outright discarded. 

Serve the audience not yourself: Last year we did a show about Micheal Scott from the show the Office (EP 289). Later in the series, Micheal quits and goes back to tell his staff about it. They are super excited because Micheal finally has a story worth hearing and they are interested in how things went down. Instead of starting at the point that immediately leads up to the interaction, Michael starts out with every little mundane part of his day. He loved the attention, but his audience hated all the filler. Know what your audience wants the hear and cut the fat that only serves your own ego. 

Expand your story collection: No doubt, people love an awesome story. They may even like it a second time. If they hear it several times, it loses power and actually can hurt your likability with others. The story will start to come across as insincere and inauthentic. Remember where and when you have shared stories with you aren’t constantly repeating yourself. 

#4 Debating others

It seems we’ve come into a love/hate relationship with debating others. Think about the pandemic, vaccine, political and social issues that have rocked the world in the last 2 years and it feels likely everyone is debating each other. I love what Benjamin Franklin said about this topic over 200 years ago. 

Say whatever you will, they’ll be sure to contradict you; and if you give reasons for your opinion, however just they may be or modestly proposed, you throw the other person into rage and passion. Though they may be unacquainted with the topic, and you are a master of it, it doesn’t matter. The more ignorant they are, the more sure they are in their standpoint. 

Well doesn’t that just describe a social media post you ran across in the last couple of days? Be willing to lose the argument to win the person  (EP 116) and not hurt your reputation in the process. 

You can grow your charm and charisma (EP 227). Listen to what others have to say and don’t expose their shortcoming. Be mindful of these traps that can hurt your likability and help have more enjoyable conversations with others. 

Make a better tomorrow. 

Help the team become problem solvers

Help the team become problem solvers

If you’ve got a problem, yo, I’ll solve it…
Vanilla Ice

No truer words can be said from one of the early 90s’ most iconic rap stars. We all have to deal with problems on a regular basis both in our personal and professional lives. It’s often said that a leader’s main job is to be a problem solver. You’re hired to fix problems that pop up in your business. While it’s a little bit more complex than that, you would do well to equip your teams to be great problem-solvers themselves. 

Helping your team increase their problem-solving skills helps them be more efficient in their job, increases their level of satisfaction in their role, reduces stress and uncertainty, and lightens your load as a leader. 

Help them change their mindset

We all have a tendency to avoid things that we don’t like, and this is one of the reasons why we put off problems that need to be solved, or we don’t address them in the right way. While changing someone’s mindset on anything takes time, you can be successful in altering their perception of the problems that are ahead of them. 

Help them:

  • Help them see problems as opportunities. Help your team see that problems are inevitable. It’s part of life and business, no matter how well we plan. Helping them with this understanding will assist them in becoming more open-minded when a problem occurs. 

  • Don’t linger on the implications of the problem too long. We can sometimes spend too much time focusing on the impact of the problem instead of focusing on the problem itself. For instance, you may have left your wallet at home and you begin focusing on how it’s going to impact and ruin the rest of your day. Instead, focus on what you need to do to get yourself fixed up for the rest of the day and keep moving forward. On the podcast, I share a story about realizing I didn’t have my wallet when I arrived at a hotel during a week-long trip with no means to get back home. It was a week of problem-solving for sure!

  • Make a list of worst-case scenarios. Sometimes it’s helpful just to see that the problem is just not as bad as you thought it was. Doing this will help you think objectively as you face an issue and begin problem-solving. In my wallet story, I realized quickly that I couldn’t linger on the issue and thinking of the worst-case scenarios actually helped reroute my thinking into some out-of-the-box ideas that successfully got me through the trip and back home. 

  • Focus on improvement. Help your team by helping them focus on what they can improve on to eliminate or minimize the problem going forward. Perhaps it’s a change in policy, additional training, or altering a process. For my wallet situation, I began the phone-wallet-keys check on myself before moving to a different location.  

Answer questions with questions when possible

One of my tried and true ways to help people grow in their problem-solving ability is to answer questions with my own reflective question in order for them to start thinking through things for themselves. 


Team member – “How do I handle this customer issue?”

Leader – “How do you think we should handle it?”

After hearing their strategy, affirm their answer or coach to redirect them towards the right solution. Sometimes lower problem-solving ability comes from lower levels of confidence in the job, not feeling equipped to handle the problem, or they don’t feel like they have the authority to address the question or scenario. This tactic in coaching helps strengthen and solidify all of those areas. 

Coaching by asking questions instead of always providing answers is very effective, but it takes more time. If the situation is dire, or of high urgency, fix the problem and then debrief afterward to help them see how they could have navigated the situation. 

Run chessboarding exercises

In Finding Leadership in Chess (EP 290) we talk about the chessboarding exercise.  It’s an activity that you can complete with others that centers around hypothetical scenarios that are rooted in reality and how you would respond to the situation. 

This is a great exercise to run with your team as you help them increase their problem-solving skills. It forces the person to think critically and strategically in order to overcome the change successfully. One of the best parts? You get to talk it through with no consequence since it’s hypothetical. Learning without the cleanup! 

Good problem-solving skills will serve you and your team well. Spend time honing in those abilities to become more effective and less stressed where you are. 

Make a better tomorrow. 

Tips to Support Your Teams Mental Well-Being

Tips to Support Your Teams Mental Well-Being

We’ve all felt the lasting impact of the last few years. A study confirmed it, we’ve gotten more stressed and feel a high level of anxiety these days. 

In order to keep people engaged and have them stick around, it’s important for you as a leader to be mindful of your team’s stress levels and well-being.  While serious treatment for mental health concerns needs to stay with the professionals, there are actions that you can take to help support and care for your team. 

Keep a high-touch communication cadence

The saying “Out of sight, out of mind” is certainly true. Think about your personal goals, desires, and best intentions. Without intentionality to keep them in front of you, they end up falling to the wayside and become missed opportunities and disappointments. That’s one of the reasons we recommend whiteboards, apps, and/or smaller physical capture points to catalog your goals, both short and long-term. 

Think of your employees in the same way, if they are working remotely or in a different location, they are in danger of being left behind and feeling disconnected from their work and from those that they work with. 

I’ve always been a fan of weekly one-on-ones, even when I led remote teams across a large geographical area, I kept a cadence of check-ins with my direct reports. The pandemic pushed me to change my communication style in order to meet changing needs. I no longer have scheduled one-on-ones, but put quite a bit of effort into connecting multiple times a week in both formal and informal settings. This has helped with a list of things not building up and makes the conversation cadence feel like we are in an office setting without actually being in the same space. 

High touch doesn’t mean quick and shallow communications. Is it appropriate sometimes? Yes, but include meaningful and deeper conversations as well. 

Some prompts to get you started:

  • How are you feeling about your workload?  Do you have enough time to get everything done?
  • How do you feel at the start and end of your day or week? (Good question to gauge burnout)
  • How can I support you or your work?
  • How are you staying connected to others?

Help your people’s well-being by making sure that they feel informed, included, and appreciated. 

Cue into the nonverbal and physical clues
We know that there is power in non-verbal communication (EP 186). People that are struggling with stress, anxiety, and uncertainty will often show signs of distress, it’s just a matter of you as a leader being attentive enough to pick up on the clues. 

Look for changes in behavior that can include:

  • Wanting to, or outright avoiding group gatherings, both in-person and virtual. 
  • Showing signs of fatigue, aches, pains, and changes in energy level. 
  • Becoming overly passive, or losing and sense of engagement.
  • Showing nervousness, irritability, and restlessness. 
  • A drop in the level of communication

As a leader, you make it easier for your people to share when you are attentive and engaged with them on a personal level. They see your attentiveness and will open up more to you. On the other hand, they also know when you aren’t paying attention and will volunteer less information and articulate less on issues and struggles. 

Allow them time to refocus, decompress and reframe

Overall, I think people are harder on themselves than they should be. I know that I am. I have a tendency to try to push through physical pain, burnout, or setbacks.

Pushing for progress is always a great approach right? Well maybe not. I had years of built of injuries from running because I kept pushing through them all and tried to quickly fix things so I could continue on. I took the pandemic time to try something new…. rest. It took a long time, but my foot, knee, and hip issues all eventually resolved themselves. Even my back started feeling better and survived a big house move. 

When you identify that a person needs some time to focus on their well-being, don’t wait for them to ask for time. Be proactive and help them get the time to take care of themself. 

  • Keep track of their vacation cadence. Encourage them to take time off and get away from work. 
  • Help spread their workload to help ease their stress. 
  • Look for efficiencies in work to help them eliminate time wasters.
  • Partner together for ways that they can delegate some work to others. 
  • Model and demonstrate how you decompress and refocus your life. 

Encourage and affirm your people that is ok to take that time needed for them to take care of themselves. Your team shouldn’t foster a culture where an individual considers it a badge of honor when they go long times without taking a break from work. The work will always be there, but the employee won’t if they reach a high level of burnout. 

An employee’s well-being is equally owned between themselves and their leader. They should prioritize their own health and mental well-being and the leader should remain committed to supporting their well-being through their experience at work. Be an impactful leader by starting small and having the intentionality to support your team. 

Make a better tomorrow.