The Mark of a Master Strategist

Master strategists are a rare breed of people.  They are able to play high level chess and make it look as simple as playing checkers. A few years ago, I started working with a vice president whose role was to head up a Latin American department for a Fortune 1000 company.  As we brainstormed different initiatives, he more than showed himself to be a master strategist.

As his coach, my job was to provide an environment where he could explore various options for resolving the issues he wanted to resolve.  As he answered questions, I learned so much about strategizing that I felt like I should pay him for letting me sit in on his “thinking time.”

If you want to become a master strategist, there are certain key disciplines to consider developing.  If you read last week’s blog, you will know that the insights on this blog and the next come from a team of very talented directors in a well known global company.

While being tactical is a practical, hands-on skill, strategy is a thinking skill.  One that can be grown and developed.

Certain personality types, especially INTJ’s, have a strong predisposition towards becoming master strategists, but the VP that I mentioned in the first paragraph, along with many other ISTJ or ESTJ VPs I’ve worked with, have grown from being master tacticians to developing a real knack for being strategic.

Here are the marks of a master strategist:

1. Master strategists free up time & then fiercely protect that time.

Strategists must have room in their schedule and mind to think.  They look for ways to block off even 15 mins just to think.

Once they free up time, they protect it, just like they would an important meeting. Time and space to brainstorm are not seen as a waste but as an essential part of success.

Without taking this first step seriously, they wouldn’t be able to move to upper levels of strategy.

2. They spend time with those who are also master strategists and those that are higher up than them.

Nothing beats being around the masters. They look around and find those who really get strategy and become a regular feature on their calendar. They ask if they can sit in on times when they are brainstorming strategies with their team and soak it all in. A master strategist surrounds himself with like-minded people.

3. They think long term.

Master strategists typically think long-term--3, 5 and even 10 years ahead. They consider how the events of today are going to impact that time frame. They think about other industry events and where they will be in the long term. In essence, they are futuristic, taking into account the long-term impact of their decisions.

4. They stay close to the company’s broader vision.

Master strategists pay close attention to the company’s broader vision and align strategies with it.  This is a great way to gain buy-in throughout the organization.

5. They cultivate different points of view.

Master strategists develop relationships with different departments so that they can get a feel for what they care about, how they think about it, the concerns and issues they have, what they consider to be successes and where they sense the future is headed.

In doing so, they are able to spot trends (see below) and think big picture.

6. They step back & spot trends.

As they get to know different departments, master strategists start to see certain themes that are consistent across the company. They see how others in the company think through things. They see things the way that higher-ups see them. But they also get a feel for what is going on in the front lines, which often the higher-ups don’t get to see as quickly as they might.

They also look at the data and see what the company wants to invest in over the long haul.

7. They plan ahead to take advantage of those trends.

Once they see the trends, they ask themselves how, in their specific role, they can take advantage of those trends.

They manage risks by first filling the facts box and sharing those facts with key executives; then, they can write a summary page so the executives know what they will be getting.

They must define what issues they are facing and be thorough with the process.

They need a robust fact base to make sure that they are solving for a real need.

Any alternatives should be fought about.

Strategic thinking is about asking the right questions: How will we win?  What is at stake?  How do you define success? What would the different departments say about this plan?

Master strategists think of all the angles so they can anticipate every question and plan for it with their team. They also make sure they are clear on what they need to execute their plan.

8. They foresee obstacles and plan ahead to overcome those obstacles.

Master strategists also consider the obstacles that are going to come.  Once they see the trends, they ask themselves what obstacles will naturally appear.

They take the list and decide how their team can best tackle those obstacles before they even arise.

9. They get validation and buy-in, paying close attention to feedback.

They consider who needs to buy in, thinking in terms of what the stakeholders value and how their plan fits in with those values.

As they implement their plan, they pay attention to the feedback they receive and make tweaks. They are aware of when it may be best to abandon the plan.

10. They anticipate the informational needs of their boss and boss’s boss.

Thinking in terms of what their boss and boss’ boss want to know to make decisions at their level, they may gain greater insights in how to think strategically.

Becoming a master strategist is easier for some than for others.  However, everyone can improve their strategic skills by recognizing the marks of a master stragetist.


Chew On This:

  • How can you become a more skilled strategist?
  • Who on your team embodies these strengths?


Ryan C. Bailey is President and CEO of a company that equips leaders to develop in-demand high-performing-teams.

8 Ways to Own Your Senior Leadership Presentation

If you are going to present to senior leaders, you need to understand that it is different from doing a presentation to your team or to peers. Senior leaders are focused on high-level decision making.  Consequently, your presentation needs to support them as they make these decisions.

Below are some tips that can be useful when presenting to senior leadership:

1. Over-Prepare.

When presenting to senior leaders, it is really important that you over-prepare.  Make sure you know not only the materials pertaining to the stated topic, but be prepared with any insights you have gained from looking at all the materials.

Make sure you anticipate their questions.  Think in terms of how the material they are presenting will help them make good high-level decisions.

Develop some thought leadership on the topic.  This can come in the form of insights that may not show up in the data you are presenting (personal insights you have gained from being closer to the front lines).   These are insights that they would not otherwise be exposed to.  A key insight would be what you foresee may be coming, based on the data and your connection to those closest to the front line.

2. Have one key message that you want to make sure they walk away with, and start with that message.

This can be the thought leadership point that we discussed above, especially if it answers the central question that senior leaders are asking.

If your presentation is based more on something you want from them, then the key message could be your request, tailored to what they value, so they can see the benefit of saying yes to your request.

Be sure to repeat this key message directly, or in a paraphrased version, during the presentation, and end with it.

3. Assume you have only half the time you were allotted. Oftentimes, presentations run long.  If you can do your presentation in half the time and still leave a lot of room for engagement, you will be seen as a winner.  You will notice senior leaders breathe a sigh of relief as you helped them get back on track.

Higher ups will look forward to your future presentations because they know you will be efficient with your words, and be able to convey a message in a fraction of the time.  This is a skill to be practiced and developed.

Be sure to have supplemental slides that you can access quickly in case they want more details from your shortened presentation.

4. Own the process.

How do the content, engagement format, and your co-presenters help move the discussion to simple, practical actions that won’t add to senior leaders’ workload?

You are responsible for all parts of your presentation.  You are responsible to move engagement towards action.  Just be certain the actions you want are simple and practical.  Senior leaders are highly busy.

You will need to be prepared for senior leaders to interrupt you and ask questions.  At other times, they will patiently hear all the details, and even ask for more.  You may not know ahead of time which way they will lean, so be prepared for either.

5. Start with a summary of the key points you have developed to meet their particular request for help.

This first slide could contain the key message you want them to walk away with, then short phrases to capture the bullet points.

Since I cannot share data about a specific company, I will give you the summary slide that I use when I do a workshop on Greg McKeown’s Essentialism.  You can adjust it for your presentations.

Some senior leaders like pithy or catchy quotes like the above; others will not.  It is really important that you tailor your deck to your audience.

Let the rest of the PowerPoint slides support this first key slide.  If your first slide is good, you may find that most of the time will be spent discussing the key points of this slide.  Take that as a positive sign.

Make sure that you lead with what is most important to senior leaders.  Since many of them will be Sensors on the MBTI, they typically will get heavily into the details of the first item and thus spend a considerably less time with the rest.  (So in the example slide above, senior leaders typically spend 40% of the time on the first quote.)

6. Focus on simple practical actions that don’t add to their already-heavy workload.

If the primary purpose of your presentation is to encourage senior leaders to take the specific actions you want them to take, then please lead with those simple action items. You can then build the rest of the presentation around those actions.

If your presentation is about relaying data and providing thought leadership from your perspective, then facilitate discussion around the simple action items they need to take to achieve the best results.  If you think about how much money is spent in everyone’s compensation package per presentation, the amount is staggering.  Senior leaders are often very busy, so it is hard to have them all in the room at one time. Your presentation time will be their time to brainstorm and make decisions.

7. Include a buffer of time for the unexpected 10%-25%, depending on your history for going over with that audience.  If it is a new audience, then focus on the overall time.

8. Once you complete the PowerPoint deck, prepare for the presentation by going through the slides with objective outsiders, not just with your co-presenters.

Have them not only give you feedback, but also ask you the toughest questions they can think of to help you prepare.

Presenting to senior leaders is different from presenting to peers and your team.  The focus for senior leaders is on high-level decision making.  The key is to orient the presentation so that it is efficient and facilitates brainstorming which will lead to simple action items.

Chew On This:

  • What is the main message you want senior leaders to walk away with from your next presentation to them?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.


*This blog is an amalgamation of a few different clients.  No one single client is being singled out.


Your Best Self In The New Year

This blog is going to be short. If you followed last week’s blog, we discussed how busy the holiday season can get, and I am discovering that is truer than I realized ;-) Many of us are looking into the new year with a desire to better ourselves.  We may have received some feedback as to what areas need to be improved.  We may also know intuitively of other areas that need improvement.

A helpful question my coach once gave me is, “If you had to replace yourself with an idealized version of yourself, what traits would your replacement have?”

So let me be clear... Since we are talking about ideal traits, we may never reach that idealized version of ourselves, but excellence and mastery can still be achieved.  For a goal to be SMART, it must be achievable.

For me, one skill my replacement would bring would be the ability to apply just the right amount of structure into coaching meetings without losing connection or movement towards the essence of what a client wants resolved.

1. Create SMART Goals

My advice is to make a list of ideal traits then consider creating SMART goals around each of those idealized traits. 

So for me, it is: In January, I will ask clients whom I sense want more structure to describe the structure they want, and I will start a process of trial and error to nail the structure they are looking for within three months.

If you create SMART goals around the idealized traits, then you can set yourself up for success by breaking those goals down into smaller steps.  Given the above goal, my steps can include:

  1. Determine which clients want more structure.
  2. Depending on personality type, phone, Skype, email, or wait until our next meeting to talk about the structure they desire for our meetings.
  3. After they share what they want, repeat what I hear them say until they feel like I’ve nailed it.
  4. Let them know that I want to nail it down as soon as possible, and if there are further tweaks that need to be made along the way, I will be happy to make them.
  5. Implement.
  6. Review and assess how it’s going with the client.

2. Get Accountability

Next step is to have accountability for the change you want to make.  How would you like to be held accountable for the realization of those idealized traits?  In my case, I have my coach. But more importantly, the client will naturally provide accountability.  Accountability would also come from what I am sensing as the structure is implemented.

3. Celebrate Your Victory

Finally, once repeatedly nailed, it will be time to celebrate.  How would you like to see yourself celebrate once you’ve achieved what’s possible to achieve, with respect to that idealized trait?

The celebration could be small, like “I will buy a couple of songs on iTunes that I have saved in my wish list.”  For goals that really impact your leadership or team, you could choose something bigger, like “I will take my wife and kids on a three-day beach vacation.”  The idea is to visualize how you will celebrate so you are further motivated to achieve that goal.

If the goal is a bigger or long-term one, consider having celebrations each time a milestone is met.

If you dream of the idealized version of yourself, you can achieve your best you.  Make small, steady progress, and you will be surprised by how different you will be by this time in 2017!

Have a fantastic holiday season and very happy new year!

Chew On This:

  • What traits does your idealized self have?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

How To Work With Someone You Don't Like

how-to-work-with-someone-you-dont-likeHigh performing teams exist when there is a high degree of mutual trust and respect.  Team members need to believe in each other’s abilities and fight to draw out the best in everyone on the team.  All members need to know that they belong. But what happens if there’s someone on the team that you just don’t like? Maybe the person is too abrasive, too blunt. Or maybe it’s the opposite: they are too passive. In order to avoid conflict, they appear inauthentic. Or maybe they are ego-centric.  Then again, maybe you can’t put your finger on why you don’t like them; you just don’t.

Whatever the reason is, you need to know that when you don’t like someone, it will affect your ability to work with them.  Your degree of trust in them, your respect for them, and your belief in their abilities will all be impacted, with the result that you are not going to want to fight to draw out the best in them.  Most of us want to spend as little time as possible around people we don’t like.

The good news is that you can learn to trust and respect them, and even believe in their abilities.

1. Get to the root of your reason for not liking them.

What is it about them you don’t like?  List the character flaws or behaviors that really bother you.

Next ask yourself, What is it about those traits that leads you to feel that way?

Is it that you have some of those traits?  Yup, ouch!  If we don’t like someone, it is often because that person has traits that we see in ourselves, and don’t like.  The good news on this one is that you can start turning your dislike into empathy just by realizing that the person you don’t like is a lot more like you than you thought.  You have a negative trait in common, and if both are willing, you can even partner with each other to overcome it.

Is it that this person has the same traits as someone who hurt you in the past, someone whom you have never forgiven? Do you seem to keep bumping into that kind of person? If so, that could be a sign that you have never fully forgiven the person who hurt you originally. Consequently, when you meet someone with similar traits, you become defensive and over-react.  The key here is to forgive fully the original person.

Or is it that you just don’t like a particular personality trait? For example, Thinkers vs Feelers.  Thinkers are about truth.  So they freeze their emotions in order to get to what they would consider objective reality.  In the process of freezing their emotions, they can come across as cold, abrasive, and too blunt.  Understandably, this can lead to conflict or disharmony. Feelers are about harmony.  They hate conflict.  As a result, they can appear inauthentic, or even manipulative in order to avoid disagreement and maintain harmony.  But this can prevent the truth from coming out. Can you see why it would be easy to dislike someone who is the opposite of your personality bent?

2. It’s okay that you don’t like them.

I know, I know... This is not what we were taught in kindergarten.  But it’s true that at the end of the day, we can work through whatever forgiveness issues we may have, we can learn to appreciate personality differences, we can even overcome our negative traits, but still not really like someone.  We may have learned to tolerate them and even to see value in our differences, but we are not ready to start hanging out with them.  That is okay.

The important thing is that you work through your stuff, while still showing them the dignity that all humans deserve to be shown.

In addition, if we are going to work with them we are going to have to up our trust, respect and belief in their abilities.

3. Increase your desire to trust, respect, and believe in their abilities.

If you don’t want to like them, you are not going to like them.  The same is true if you don’t want to trust, respect, or believe in their abilities.  Sometimes we need to list reasons why we should increase our desire for the good of the team.

You can go about this in several ways. One staple of mine is to ask a “What if” question.  “What good could come if...” So in this case it is, “What good could come if I trust, respect, and believe in their abilities?”  Notice I did not say what good will come.  I said what good could come.  Here is where you want to list as many good things as possible that could come.

If I am struggling to want something that I don’t want, and I ask a “What good could come?” question, I may come up with only 2 or 3 things, and not feel really satisfied.  Try Googling “Benefits of trusting a co-worker,” and you will find more to add to the list.

You can also think of the benefits you yourself have received from trusting, or respecting, or believing in a co-worker, and add those to the list.

The idea is to come up with as many things as you can think of until you see your attitude changing to one of increased desire.  Then, as that desire gets fueled, you won’t be able to stop yourself from taking action.

4. While you are working on the first three, know that you don’t have to act on what you feel towards them.

One of the things that I love about emotional intelligence training is seeing how someone learns to increase their emotional self-awareness and then learns to regulate their emotions on the fly.  The confidence that comes is tremendous.  You can learn to do the same.

As you learn, stay away from gossiping about them.  Instead, actively find ways to help them.  That will help you to change your attitude towards them.

5. Find the good in them for you and the greater whole of the team.

They are on the team for good reasons.  Identify and focus on those reasons and you will find yourself able to handle the less desirable traits much better.

6. Set boundaries with clear upfront communication.

If part of why you don’t like them is that they “push your buttons,” then know that you are not their victim. You alone are responsible for your response to those buttons being pushed.

Read some blogs or books on boundaries, and learn some basic techniques for minimizing your exposure to toxic behaviors.  One of the biggest ones I have learned is to use clear upfront communication, like speaking in terms of, “When you do X I feel Y.”  Notice you are not telling them what to do. Instead, you are making them aware of your response to their behavior.

If they don’t want to do anything about X, then you can step it up a notch and request a change in the behavior. Or you can say “If you don’t want to stop doing X, then I am going to leave the room for a bit and consider how we can find a different way to communicate. You have a lot to offer this team and I don’t want to let my response impact the success of this project.”  In other words, fully own that it is your response you're working on, and then take active steps to work on it.

7. How do those who work successfully with them interact with them?

Are there some on the team who work better than you do with the person you don’t like?  If so, what are they doing that’s different?  Adopting some of their techniques can be helpful.

8. Celebrate the times when they are displaying likeable behaviors.

During times that they are doing things that are much more likeable, recognize it and celebrate it.  “I really love it when you do ABC." That type of emphatic acknowledgement could go a long way towards long-lasting behavioral change.

9. Radical idea #1: Choose to work on a really tough project with them.

People who work on something really tough together tend to bond better.  It also helps to draw out the interpersonal dynamics more, and that forces you to deal with them more quickly since the tough project needs to be accomplished.

10. Radical idea #2: Find ways to laugh with them.

People who laugh together start to like each other more.

I remember watching a really funny movie when I lived in New York.  After the lights came on and audience members made eye contact as they left the theater, it was obvious that they felt warm towards each other.

On a team, that warmth develops into a real liking of each other.

If you don’t like someone on your team, you have the choice either to be stuck with them, or to find ways to make the most of the relationship. The person you thought you never would like may become one of your closest co-workers. Stranger things have happened!

Chew On This:

  • What will you do to escape the sense of being stuck with someone and, instead, make the most of the relationship?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

*This blog is an amalgamation of a few different clients.  No one single client is being singled out.

You Won't Be Promoted Until You’ve Prepared Your Successor

preparingyoursuccessorTime and time again, talented, capable executives get passed up for promotions because there isn’t anyone to take their place. When speaking to their bosses I often hear things like, “I need her there... Who else can do what she does?” and “If he got promoted, it would leave a huge vacuum.”

We are coming to the end of a new year, a time when many of us are thinking about what goals we want to achieve in the new year.  One of the top goals I hear being expressed is to be promoted.

If that is your goal, then please consider which of your team members you will train to succeed you.  Also consider how you will train them.

Here are some suggestions:

1. Speak to your boss and key stakeholders about what they would like to see in the person who takes your role.

Your successor will need support from key stakeholders, including your boss, if the transition is going to be a success.  A conversation with them ahead of time will allow you to gain buy-in from them as they see the traits develop in the person you will be choosing.

2. Create a job description based on the reality of your role.

How much of the original job description is what you do day in and day out?  Writing a realistic job description will help your successor tremendously.

Be sure to focus on what is the most essential part of the role and what are the soft and hard skills necessary to succeed in the role.  Also emphasize the appropriate points which key stakeholders said they wanted.

A question I sometimes use with the executives I coach is, “If you could hire a more idealized version of yourself to take over your role, what characteristics would they have?” (BTW- your answers to that question are great for determining what goals to reach for while you yourself are in the role.)

3. Determine who will be your successor and get their buy-in.

After you have the job description, look at your team.  Who is likely to be able to match that description and exceed it?  It may not be the direct report who is excelling the most.  Be sure to think through who has the best potential to far exceed the job description.

Then go and see if that person is interested in being trained to take your role.

If you have a huge role that needs to be broken up (and your management supports that decision), then focus on a couple of successors.

If the best person to take over is not a part of the current team, be sure to keep your direct reports informed.  As you bring the new person in, help your direct reports understand your rationale, and explain how they can help the new leader succeed.

4. Train incrementally.

Give your potential successor opportunities to really stretch their skills.  Have them assume much more of a leadership role than they have had in specific projects.  Coach when necessary.  Then have times to debrief afterwards.

5. Create milestones.

Your successor will probably want to know when they will be viewed as being ready to assume the leadership role.  The more tangible you can make these milestones, the better.  This will help stakeholders to buy in even more.

6. Focus on the future.

Assume that the current problems your team is facing will be resolved, and that there will be new ones in the future.  What principles of problem solving does the team need to learn in order to make more effective decisions?

Moreover, think about where the overall organization is heading.  What are some key things your successor needs to know and do in order to align with the greater company’s focus?

7. Consider that your successor may not be a clone of you.

There are times when replicating yourself is advantageous, and there are times when having someone different from you take over is exactly what a team needs to move to higher levels of cohesion and performance.  What do the team and the overall organization need for this next step?

8. Communicate to your team early that a change is coming.

Knowledge of an imminent change can often lead people to fear the unknown.  You can minimize this fear by informing your team as soon as it is appropriate, to help them adjust.  Also, be clear about expectations, so that everyone knows what to count on.

9. Use job shadowing.

Your successor needs to know that they are being watched by those above the team members.  They need to learn to be the leader before they get the position.

Job shadowing will help them see a template in you.  If they are a different personality type than you are, and/or have different gifts than you do, then use some of the shadowing time to discuss how they would have handled things in their style.

10. Set your successor up for success.

Determine what win your successor could have before assuming their role that would help the team to fully embrace their leadership?

However you can set them up for success ahead of time will pay dividends in a smooth transition.

11. Offer to be a mentor/coach for awhile after they’ve assumed your role.

Some successors may not come to you as much as to others.  However, it will be great for them to know that you are there until they get their legs under them.

Succession is key to getting promoted.  When you have a replacement, your boss and others above you will look for opportunities for you.

If there isn’t someone to take your place, don’t be surprised if getting your next promotion is more difficult than you thought.

Chew On This:

  • If you could have a more idealized version of yourself take over your role, what characteristics would they have?


Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

*This blog is an amalgamation of a few different clients.  No one single client is being singled out.

MBTI Bite: How To Pick Up Someone's Personality Type Over The Phone

mbti-bite_-how-to-pick-up-someones-personality-type-over-the-phoneJust think of what it would be like if you could figure out a new stakeholder’s personality type while you speak to them on the phone. Think of how quickly you could connect with them, tailor your dialogue to their preferred communication style, and even know how to balance their weaknesses so that they feel empowered to stay in their strike zones.

It's possible.

Myers-Briggs is the most popular and most researched assessment in the world. It breaks down personality types into four dichotomous pairs.

1. E vs I, Extrovert vs Introvert.

You know the person on the other end of the telephone is an E if they consistently talk things out with you. We E’s are notorious for thinking as we speak. We've also got a case of verbal diarrhea. That is, we are verbose.

I’s, on the other hand pause, think things out and give more concise, formed answers. They also tend to process new information internally instead of with others.

2. S vs N, Sensing vs Intuition.

S’s, or Sensors, are 75% of the population. So when in doubt, you can guess that the stakeholder you are speaking to is an S. But another way to know is if they speak in specifics. Do they give detailed descriptions as they lay out information? Do they talk in more tangibles (sights, smells, sounds) than in abstract concepts?

You know you are speaking to an N, or Intuitive, when they focus on the big picture. N's often think broadly, basing their ideas more on intuition than sensory cues. N’s also love new ideas and possibilities.

3. T vs F, Thinking vs. Feeling.

T’s, or Thinkers, can be spotted because they talk about the logical implications of things.

F’s, or Feelers, may first talk about a task but will often interject with the impact the project will have on the people.

4. J vs P, Judging vs. Perceiving.

J’s or Judgers, feel more comfortable once a decision is made. Over the phone, you will sense them wanting to lock down a decision.

P’s, on the other hand, like to keep their options open. It will be harder to nail things down.

Here is a cheat sheet that gives you all of the above in one page:



Once you can pick off the letters, go to and get detailed descriptions that will help you get them better.

Even if you can't nail all the letters use this cheat sheet to tailor the way you communicate with them not just over the phone but in email too.

Chew On This:


  • How can you implement this mindset into your phone calls today?


Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

*This blog is an amalgamation of a few different clients.  No one single client is being singled out.