Archives For Clarity

The Key To Making Big Decisions

September 30, 2014

Making decisions is what leaders do, right? Then why is it when we’re faced with making our own career decisions we all of a sudden become terrible and overwhelmed decision makers?

If you’re like me, when faced with making big decisions, you can feel like you’re on a roller coaster ride. One minute you’re up, the next you’re down and before long you’ve spun and flipped so many times you’re not sure which way is straight. I’ve received and given lots of cliche advice, “You’ll know when its time.” “The right door will open up.” “It will all work out in the end.” I appreciate these hope filled statements but at the same time they don’t offer much concrete help. When you’ve been on the roller coaster ride, what you need is a clear path forward and more importantly a clear process to understand how and why to choose the right path.

When I was leaving my last role as an executive in a start up retail coffee company, I was torn. I enjoyed what I was doing but I felt like something was missing that I couldn’t put my finger on. One day it clicked, I need to prioritize what I’m looking for in my career to help me make the decision of whether I should go or stay. If you’ve read my blog long enough you’ve started to notice that I love to prioritize. It’s the single most helpful thing I’ve found to more effectively manage my life and leadership. It’s a process that can be applied to anything, including how to make a really big career decision. Beyond myself, I love helping clients walk through this process; clarity is a powerful tool.


There are so many factors that go in to making a big career decision. It’s easy to worry about making sure you’re doing the right thing and plagued by the thought of what if I made the wrong decision. The last time around I took myself through an exercise that I felt was very valuable and worth sharing. This exercise forced me to prioritize 10 important factors that go into any big career decision. The key is that you have to prioritize these factors for yourself. What’s most important to you will drive the big decision.

The 10 Career Factors

  1. Control – How important is the ability to envision the future and make decisions to build towards that future? Are you comfortable with implementing someone else’s vision or do you need it to be your vision? Do you need an environment with more freedom?
  2. Schedule – Do you have the desire to chart your own course and dictate the schedule? Want to work 3, 15 hour days, and golf the rest of the week? Are you good with constantly changing hours? The nine to five grind works for many people but others need more flexibility.
  3. Faithfulness – Do you enjoy using and maximizing your talents to better those around you? Do your gifts align with the work before you? Some careers more than others will use what you have to bless, encourage, and make the world around you a better place.
  4. Money – What kind of salary/wage/future do you want to create? What kind of financial margin are you hoping to build? How important is the right salary to your next career move? It’s not always about the money and its priority changes in different life stages.
  5. Passion – How important is it that your work align with your passions? Are you ok finding your passion after you leave the office? Or, if you’re not carrying out your deep convictions on a daily basis, do you wither? If you can’t quit thinking about it positively, that’s a good sign it’s important to you.
  6. Happiness – Are you looking to your career as your main source of happiness? Is it possible to have a job you aren’t happy in but you can live with it? For some if they don’t come home smiling about the day then it’s devastating.
  7. Fulfilling – When you wrap up your day how important is it that you feel personally fulfilled? How critical is it that your desire, expectations and reality are aligned? Nothing is perfect but you go to bed with a full heart, a good day is a meaningful day.
  8. Family – Do you love to have your family involved with your work? Does the thought of working with family make you cringe?  How important is it that your family is intimately involved and engaged in the work? Not prioritizing this high isn’t a statement of your lack of love your family, it just means you and they don’t benefit from working together.
  9. Team – Do you like to fly solo or do you need the collaboration of a good team to survive?  How important is the team around you? The people around you matters more to some than others.
  10. Community – How important is it to be connected to a larger group of like-minded people? Are you particular about your neighborhood or the type of people you want to rub shoulders with outside of the office? Or, are you so adaptable you can make it anywhere? For some it’s all about location, location, location.

No job is perfect. No career is executed flawlessly. No relationships are absent of strife. The goal here is not to remove every difficult situation from your life. The goal IS to understand how you’re made and how you thrive so that when making a difficult decision you have a prioritized rudder. For some, making a big salary is overrated so that slips down the list while being happy is a the top. For others it’s all about the team and they could care less about the long hours or lack of personal control. Still others find themselves withering away if they aren’t living in their passion every minute of their life.

There is no cookie cutter answer for everyone but there is a better answer for you. Rank these 1-10 and then evaluate your current career and future opportunities in light of them. One of my priorities is to help you and other leaders get clear on the most important things. Clarity is never overrated.


I’m a casual poker player.

Say what you will about poker, the game itself can be a very useful allegory for life in the business world. When you play a game like poker, you have a set of cards that are dealt to you. Every move in the game is about evaluating and measuring risk. In fact, on the card table, gambling can be seen as an investment in your available resources and the longevity they may have against the other potential hands at the table. As you weigh the strength of your hand, you will inevitably (or should inevitably) reach a point where a hand you’ve been dealt is incapable of competing, and you will have to fold your hand.

The same dynamic can be true for leaders. At some point, every leader has to face the reality of an underperforming facet of the organization, and sometimes after weighing the risks and the benefits, a cut is necessary. There’s a very good reason why we call it “cutting your losses”: it’s painful. It can feel personal. It’s never easy.

Knowing when to cut your losses is the real challenge. Whether it’s an unsuccessful product launch, an obsolete department within your organization, or even an otherwise productive employee who has developed a toxic attitude – often, we will “stay the course” assuming that if we keep our hand to the plow, we’ll be able to navigate through the situation. As we consider the investment we’ve put into these things, it seems better to push through rather than to take a loss. This could be your downfall.

Two kinds of mindsets when facing a major loss

How we think about the situation has a lot to do with how we come up with a solution. Psychologists identify two kinds of mindsets when facing a major loss:

  • Prevention Focus – concerned with what is lost if we don’t succeed.
  • Promotion Focus – think of goals in terms of new potential gains.

If you adopt a prevention focus, you’re more likely to see all the investments you’ve committed to getting where you are today, making it difficult to cut your losses. If you adopt a promotion focus, you’ll be much more likely to see the cuts as an opportunity to reinvest.

While both positions have merit, studies show that people will more often instinctively take a prevention focus because the effort they’ve invested is a tangible factor in the decision. In other words, they’ve shelled out the money, time, and effort, and they hate to watch it go down the tubes.

Often the promotion focus is the less obvious, but much more fruitful, position. The person sees that there is still money, time, and effort that are yet unspent, and those resources would be better allocated to other investments, rather than continuing to send them down the drain. This is the focus of the visionary.

Knowing when to fold your hand and cut your losses is a great challenge that can’t be taken lightly. Often, the decision to keep going can have as big an impact on your life or your business as the decision to cut. When you face the question of cutting your losses, step back and know your focus: prevention or promotion. It can make all the difference.



You know that feeling?

Something is off. You aren’t in sync with your boss. Your team seems fragmented. Time and energy feels wasted. There might be a major defining moment that is at fault or it could be incremental deterioration. Regardless of the source, it’s not ideal and a sustained disconnect undermines you, your company and any healthy forward progress.

What’s the culprit? And more importantly, how do you fix it? Life would be easy if the blame game was black and white. In my experience it’s never been that easy though. Broken relationships and fragmented teams are often the result of many factors. It’s always the leaders responsibility to deal with but not always their fault.

[Tweet “Broken teams aren’t always the leaders fault but they’re always the leaders responsibility to fix.”]

Diagnosing the broken connection

The team doesn’t know the vision. When your team doesn’t understand or know their personal connection to the vision you create a disconnect. Instead of rallying behind THE vision they start to create their own to fill in the gaps. Is this your story? If so, don’t settle. Fight (respectfully) for a clear vision and if you’re the leader, listen, so that you can provide the clarity your team needs.

Everyone is in it for themselves. This could be the leader that overlooks the needs of the team or it could be a rogue team member that doesn’t lift a finger beyond their job description to help out.

Reality is ignored. The very nature of a vision is that it lives in the future. It’s something to be achieved and navigated towards that is different then the present reality. BUT…it doesn’t mean we get to ignore the present reality. Leaders need to be honest about the present situation or they’ll loose their team. Painting a false sense of utopian reality doesn’t help anyone. We need to be honest about the present struggles as we paint a picture of a better future.

Company values are all talk. Knowing and living your company values should be a no-brainer. You have them for a reason, right? However, if your company values are nothing more than words on a paper or platitudes dished out in a meeting then you’ve got a case of hypocrisy. Your true values are what you do day in and day out. When they’re aligned, watch out world. When they’re not, a credibility storm is brewing.

My way or the highway. Humility might be the most powerful way to unite a team. When established leaders are out of touch or new leaders are arrogant you build a culture of isolated superheroes. A team where everyone wants to lead as long as it is their idea, isn’t really a team.

Feeling disconnected is an awful spot for everyone. No one wins. How can you fight for clarity and lead your team to be more connected?


How do you measure clarity in your organization? Is it as simple as asking everyone to regurgitate the company mission statement? Providing clarity is the hardest yet most necessary work of any leader. We usually don’t like to ask the questions because we don’t really want the answers. It takes time and might make more work in the short term. Here are twenty-one questions I dare you to ask your team this week. Allow for anonymous answers if you think that will give you the most helpful and unbiased information. Then schedule at least a half-day out of the office on your own to study and organize the answers. It might be painful, it might be encouraging, but regardless it will be insightful into the clarity your team has and where you might need to emphasize your leadership attention over the coming months.

Image © Nate Smidt

Mission Clarity (WHY?)

  • Why does our organization exist?
  • What is the single most important thing we do in the world?
  • How would you articulate the company mission in your own words?
  • How do you personally connect with the mission? 

Vision Clarity (WHERE?)

  • Where is our company headed?
  • What should the organization look like in three years?
  • What are the top three objectives of the company over the next year?
  • How does the vision of the company inspire you on a regular basis?

Leadership Clarity (WHO?)

  • How would you define the leadership culture of our company?
  • How many bosses do you have and do you know who they are?
  • On an average day, how many people are delegating tasks to you?
  • Do you have a defined path for personal growth and leadership development?
  • How is your supervisor developing you for future responsibility?  

Strategy Clarity (HOW?)

  • What are our three most important strategic initiatives right now?
  • How are we going to accomplish these initiatives?
  • What are we doing that we should not be doing as a company?
  • How do our day-to-day tactics align with the vision of the company? 

Numbers Clarity (WHAT?)

  • What are the most important numerical metrics we measure?
  • Do you have good information and data regarding the metrics?
  • How do you define success in your job?
  • Do you know the financial goals of the company?

[Tweet “21 Leadership Questions You Can’t Afford To Avoid”] 

Are you willing to take the risk? The more dead honest you and your team are, the more helpful it will be to your future. If I can be of any help with a Clarity Session please let me know. Go for it.


I got stood up at lunch yesterday and while I sat there, checking my phone to pass the time, two guys next to me were having a clarity crisis conversation. Trying to figure out what was wrong with their boss. “Is he stupid? Does he not care? Is he full of $&*T?” They bounced back and forth between talking about how this place is better than all their previous jobs, and trying to understand the severance policy of the company and how many weeks of pay they might be entitled to. You might say this is just the reality of business these days but I don’t think it is overstating things to call it a crisis. A clarity crisis that is eroding away at the company’s bottom line and the emotional health of its people.

Clarity doesn’t mean you know the future. Clarity doesn’t automatically put an end to bad leadership or selfish employees. Clarity does better your chances of creating a unified and prioritized team that spends their time thinking about how to make the company better rather than their exit strategy.  

Three keys to defining and building clarity

Clarity is the antidote to feeling lost or stuck. Here are three important ways to ensure clarity within your organization.

1. Clarity is a shared reason for being. The most philosophical of the bunch for sure, but it’s a reality you can’t avoid. People are only motivated for so long by activities, you need to dig deeper into why your company exists. How is it uniting people together towards a common goal? More and more people want to make a difference, a difference that resonates with who they are. What an amazing opportunity to help our teams make these connections to the why of what we’re about. 

2. Clarity is a shared vision for the future. We all know that every vision we have does not come true, but without a vision we can’t lead anything. When you don’t know where you’re headed, you loose perspective, you loose passion, you loose the joy and satisfaction of a job well done. Your work becomes rote and disconnected from the future you envision. Work with your team to explore, understand and build a shared vision of the future together. As you do, you’ll find the buy-in and commitment begin to increase.

3. Clarity is a shared strategy for execution. When the rubber meets the road, every person on your team will have the tendency to interpret the best path forward through their own lens. A great vision is one thing but a lack of clarity develops most quickly in the execution. There are always different methods to attack an opportunity but it is hard for the same team to deploy different methods. Investing in this will take your company to that next level as everyone operates from the same playbook.

None of this is easy work but it’s worth it. How can you drive more clarity within your organization today?