Helping Project Managers to Help Themselves

The Scenario: 

1. Anita promotes Ed to a leader of leaders position from a position leading a small team of individual contributors.
2. Ed is excited about the increase in responsibility and is determined to show Anita he can handle the job.
3. Ed’s calendar gets bombarded with meetings and his to-do list grows.
4. Ed’s leadership team grows dismayed with Ed’s lack of responsiveness, urgent 3 a.m. email requests, and canceled one-on-ones.
5. Ed’s daughter is disappointed with dad missing yet another Saturday soccer game.
6. Ed misses a critical deliverable for Anita, forcing her to have an uncomfortable discussion with her boss. Anita takes the blame, not wanting to throw Ed under the bus.
7. Anita’s offers to coach Ed go unheeded because Ed is too busy to be coached.
8. Anita makes the difficult decision to tell Ed he will be demoted back to his old job.
9. Ed decides to leave the company for another job, rather than get demoted.
10. Nine months later at his new company, Ed gets promoted and repeats steps two through nine. Wash, rinse, repeat.

The Message: Unfortunately, Ed’s situation is all too common for those scaling up to a leader of leaders role. Increases in demands can’t be met simply by working longer and harder; at some point, an important commodity—time--dries up, because the leader can’t get everything done and keep balance. Just like the little pig that built the brick house the big bad wolf couldn’t blow down; the leader needs to build strong time-management skills early so he can better scale to the demands a leader of leaders faces. Waiting to become a leader of leaders (or worse, not building strong time management skills at all) means the leader won’t be sustainable as a scaled-up leader.

Want to get better at time management? Give these nine time-management habits a look:

1. Express to-dos in terms of deliverables – I like to think of this as “do vs. done.” What needs to be produced for the to-do to be satisfied? It could be a presentation, email, or meeting notes. Articulating the deliverable helps you better focus on what has to happen to satisfy the deliverable and reduce distractions in getting to “done.”
2. Stop at good enough – When defining your deliverable, think of the minimum requirement that needs to be met, create your deliverable to meet the requirement, then STOP. Spending extra over-achiever time on a deliverable only means you have less time to work on other things. Under-promise and over-deliver is fertile ground for wasted time. Be clear on what you need to produce, do it, then move on to the next deliverable.
3. Put anything that consumes your time on your calendar – Most people I’ve worked with use their calendars pretty much exclusively for meetings and treat time to get things done as off-calendar activity. Bad move. If something consumes time in your day, it deserves to be scheduled in your calendar. I schedule everything, including work time, personal activities, socializing with friends, exercise time, and family commitments.
4. Immediately schedule short-term to-dos on your calendar – Suppose you are given an action item to produce an important deliverable by end of the week, and you accept the item without any idea when you’ll get it done. As a result, you’re not only likely to work extra hours, but the deadline hangs over your head. Put it in your calendar right away with a realistic estimate of how long it will take. This may mean moving other lower-priority things around or could mean additional hours, but at least you’ve scheduled the work in.
5. Block out some regular time to work on important but not urgent tasks – I’d place a wager that you’ve got a list of action items you’d like to get done but never get the time to do. Block out some time on your calendar on a recurring basis to work on the important but not urgent items.
6. Put a “what I got done” meeting on your calendar at the end of your work week – On Monday mornings I plan out what I want to get done by the end of the week, then put a Friday 5 p.m. meeting on my calendar listing out those things I committed to getting done. Just remember to schedule the time during the week to get those items done.
7. Be realistic about what you put on your calendar – If you schedule time for a task on your calendar thinking there’s not a snowball’s chance in a hot oven you’ll get it done, you’re setting yourself up for failure. You need to respect your calendar as credible, otherwise, you won’t follow it. Be realistic about how long something will take.
8. Reward yourself with a bit of blue-sky time – I have a two-hour recurring appointment in my calendar that I call “blue-sky time.” I can use my blue-sky time however I want; maybe it’s working on an idea for a new book, going to Costco, meeting a friend for coffee, or watching a movie. Yours may be longer or shorter or a different frequency; it’s totally up to you.
9. You own your calendar, it doesn’t own you – Look, stuff happens that may mean you’ve got to defer a meeting, move a deliverable or burn the midnight oil. By all means, move things around, but make sure you’re not chronically pushing things off due to poor planning.

The Consequences:  By not taking intentional action to manage your time, your consequences could include:

• You’re less effective – Not managing your calendar well means you get less done, it takes longer to get things done, or you steal time from other areas of your life to get things done.
• You’re not sustainable – As you continue to scale as a leader and your problems get bigger, the importance of keeping a disciplined calendar grows. I’ve seen way too many leaders burn out when they took bigger jobs because they didn’t have good time-management skills and worked harder versus smarter.
• You’re limiting your own advancement – When a leader’s time looks out of control, his promotability can be impacted. The leader’s boss could see him as incapable of handling additional responsibility if he is already hanging on by a thread.
• You’re negatively impacting your succession plan – If a leader’s followers see the leader with a poor quality of life, difficulty keeping up with commitments, or chronically missing meetings, why would they want a job that looks miserable? Attracting the very best as a successor means making the job look sustainable.     

The Next Steps: 

1. Commit to getting better at time management.
2. Get an “as-is” picture by putting everything that consumes time in your calendar.
3. Assess yourself using the nine time-management habits and decide which ones you need to work on.
4. Pick the top three habits and commit to working on them, then the next three, and so on.
5. Don’t slip back into old habits, particularly when things get really busy.

The Scenario: 

• Jake is sitting alone in his luxury penthouse overlooking Central Park.
• Jake looks down at his scribbled notes from his doctor visit. Cancer stage 4… too late for chemo… weeks to months left.
• Jake’s wife left 20 years ago after his affair. She’s since remarried and cut off all contact with him.
• Jake tries to call his kids, but neither picks up. They won’t talk to him and haven’t since the divorce.
• After Jake retired from his job as CEO, the coworkers he thought were his friends stopped calling.
• Jake takes out a pen and paper and writes “My Legacy” at the top.
• Jake stares at the blank page, pen ready to write, mind unable to come up with anything.

The Message: You may know a Jake, someone who is in their later years, and unable to point to anything significant other than his or her career and its financial fruits. For some, this may be their definition of contentment. In my years of experience, though, I’ve seen way too many people look back on their lives with regret; not acknowledging those things that are really important earlier in life.

It’s not too late to avoid being a Jake. It takes defining a practical and sustainable purpose statement--the north star that guides your actions. Then living it.

Not sure where to start? I’ve created a contentment assessment to help you think through areas in your life that are most important to you. It helps you develop a practical and sustainable purpose statement to guide you when to say yes to some things and no to others. Get started by downloading the assessment and doing the following:

• Acknowledge and understand each of the nine contentment areas:

1. Career Contentment - How content you are in your current and future career potential
2. Family Contentment - How content you are with your family life
3. Health Contentment - How content you are in your physical and mental health
4. Friendship Contentment - How content you are with relationships built and maintained with friends and loved ones
5. Financial Contentment - How content you are in your current and future financial status
6. Leisure Contentment - How content you are with quality time spent on leisurely activities
7. Spiritual Contentment - How content you are with your spiritual life
8. Giving Contentment - How content you are with your pay-it-forward giving
9. Legacy Contentment - How content you are with the legacy you are leaving behind should you die today

• Assess how important each of these contentment areas is to you.
• For areas that are extremely or very important, define your contentment goal and what you need to do to achieve it.
• Construct your purpose statement based on extremely or very important areas like: “Have a fulfilling and sustainable career with fair and equitable compensation BUT not at the cost of friendships, leisure, and life experiences.”
• Hold yourself accountable (or work with an accountability partner).

The Consequences:  By not taking intentional action to define your purpose statement your consequences could include:

• Time/priorities imbalance: Things you think are important don’t get the attention they need.
• Burnout: Too much work at the expense of other areas isn’t sustainable.
• Relationship neglect: Other people in your life don’t get the attention they need/deserve.

The Next Steps: 

• Download and complete the contentment assessment.
• Create your purpose statement.
• Be patient with yourself; it may take some reflection time to come up with a statement that energizes you.
• Live it, even if you need an accountability partner to do it.

Friday looked to be like any other day.

I got up, had breakfast, and left the house around 8:30 for a day of meetings. We had planned on having another couple over for dinner that night and a day trip with our son on Saturday. About noon, Patty called me saying she had a pain in her abdomen since getting up and it was getting worse. I asked her if she wanted me to come home. She told me she didn’t need me home, but that we should probably cancel dinner in the event she had something contagious. I was out for a few more hours and came home to her sitting on the couch, saying the pain wasn’t going away. Her temperature was 101. We talked to a tele nurse who suggested it might be an infection and that we should go to urgent care. After a short wait we got checked in. The pain continued on, now accompanied by nausea. They ran blood tests then, after seeing the results, decided to do a computed tomography (CT) scan of her abdomen. What did the blood tests reveal? Why the CT scan? What were they looking for? What’s going on? These questions raced through my mind as they took Patty away for the scan. About ten minutes later she came back, where we sat and waited for about two hours; Patty’s pain stubbornly persistent along with the nausea. Then the doctor came in.

“There’s some stuff going on,” she said as she came into the room. In that moment I don’t know how many thoughts went through my head. “It’s appendicitis,” she said. “We’re going to keep you here overnight and get you in for surgery in the morning. Pretty routine.” A huge wave of relief came over me. Certainly, the fact that Patty was going to need surgery wasn’t good news, but on the spectrum of bad news in my head this was about the best bad news we could have gotten. She stayed overnight, then around 1:30 in the afternoon went in for a laparoscopic appendectomy, where they made three small incisions in her abdomen and, using telescopic rods and a video camera, removed the angry appendix. We were back home by 5:30PM, only four hours after the surgery, where she began her recovery.

I am writing this on Sunday, the day after her surgery. She is resting comfortably and has eaten, showered, and put on her makeup. I am so thankful that it wasn’t more serious and that she is going to be back to normal in no time. What the events of the last couple of days did remind me of, though, was two words that we as leaders need to remember:

Keep perspective.

In my career I’ve had plenty of times where I thought the whole world was crashing around me. Whether it be a slipping (or failed) project, difficult issue with an employee, or totally unforeseen issue that consumed my time, in nearly every circumstance the crisis was dealt with and didn’t impact my long-term career trajectory. I’ve had a number of times in my career where I was “reminded” that what I was dealing with was minor in comparison to major life issues such as losing a loved one. Losing my sister to cancer at age 54 was a massive wake-up call to calibrate the crisis of the day and keep perspective on problems we deal with.

Now I’m not saying that we as leaders should be tone deaf when problems arise; by all means we need to address issues and not put our heads in the sand. What great leaders do, though is address issues focused and deliberately without creating additional stress along the way.

Through my career I’ve learned to ask myself three questions to help me keep perspective when dealing with issues:

1. Will the crisis impact me in the future or will I have long forgotten about it a year from now?
2. Will someone be harmed in any way because of the crisis?
3. How does this crisis compare with things like sickness or losing a loved one?

As leaders, it’s easy to get consumed by the crisis du jour and allow it to wreck your day. My ask to you is that you keep things in perspective and ask yourself the three questions when you’re dealing with you next crisis. Hopefully it will give you some peace that, while the crisis is important, it may not be as earth-shattering as it feels in the moment.

Recently I wrote an article about creating a sustained lifestyle. In the article I introduced a concept which contrasts achievement (doing something meaningful that accomplishes a desired result which gives you joy) and stress (the degree of mental, physical, or emotional strain undertaken to achieve a desired result). In the model I define four different lifestyles driven by achievements and stress, as follows:

• A frustration lifestyle is the result of high stress accompanied by low achievement. Think burning the midnight oil on projects that get cancelled last-minute or never used.
• A boredom lifestyle is the result of low stress accompanied by low achievement. Think getting up every morning with nothing to do.
• A burnout lifestyle is the result of high stress accompanied by high achievement. Think successive strategic projects with demanding customers, a dysfunctional team, and irrational management.
• A sustained lifestyle is the result of low stress accompanied by high achievement. Think volunteering for a cause you’re passionate about on your work terms.

As I’ve thought more about the achievement/stress concept, it’s occurred to me that the push-pull of achievements and stress apply to more than a person’s career or vocation. It can apply to elements such as family relationships, health, and finances. You can have high achievement/low stress in your career, but if you have low achievement/high stress in another area of your life, your overall contentment level is adversely impacted. It’s not enough to manage achievement and stress only in your career or vocation; it needs to be managed in other areas of your life as well. Given so, I adapted the good-enough contentment model I created for my Behind Gold Doors-Nine Crucial Elements to Achieve Good-Enough Contentment book to include achievement and stress as driving factors. I tested the model on myself (I ate my own dogfood as we like to say at Microsoft) and was surprised at the clarity I found in defining what good-enough contentment means to me. So, here’s the revised model, explained step-by-step:

• In the good-enough contentment model, there are nine crucial life elements that holistically reflect a person’s life, as follows:
  • Career Contentment - How content you are in your current and future career potential
  • Family Contentment - How content you are with your family life
  • Health Contentment - How content you are in your physical and mental health
  • Friendship Contentment - How content you are with relationships built and maintained with friends and loved ones
  • Financial Contentment - How content you are in your current and future financial status
  • Leisure Contentment - How content you are with quality time spent on leisurely activities
  • Spiritual Contentment - How content you are with your spiritual life
  • Giving Contentment - How content you are with your pay-it-forward giving
  • Legacy Contentment - How content you are with the legacy you are leaving behind should you die today
• In column A, indicate the importance to you for each contentment element:
  • Extremely Important
  • Very Important
  • Somewhat Important
  • Not so important
  • Not at all important
• In column B, note for each contentment element when you feel a sense of achievement. For example, in the Giving Contentment element you may feel the greatest sense of achievement when you are able to see first-hand when someone’s life situation improves when you’ve given your time or money to help that person.
• In column C, note for each contentment element when you feel stressed. For example, in the Health Contentment element you may feel stressed when you weigh yourself and see you’ve gained ten unwanted pounds.
• In column D, write an honest statement of what your contentment goal is for each element, taking into account how you maximize achievements listed in column B and minimize stress listed in column C.
• In column E, define specific actions for each element you need to take to get from your current state to your contentment goal in column D.

As you work through this model there are a few considerations for you to ponder:

• Focus on the extremely and very important elements - You can certainly have goals for all the areas, but don’t spend time on an element that is less important at the expense of one more important to you.
• Be ambitiously realistic - Create goals and actions that are within reach and challenge you, but be careful about putting things down that deep you down know you’ll never achieve.
• Be brutally honest with yourself – If building a legacy isn’t important to you then say so. The goal isn’t to make every element important, but to consider each element then make the conscious decision whether it is important to you.
• Recognize that priorities change over time – As you get older, some elements that you felt weren’t important may now be much more so. I’ve certainly found that elements like legacy, giving, friendships, and leisure are more important to me now than when I was in my twenties.

Maximizing achievements and minimizing stress across your life is critical to achieving good-enough contentment. Take some time to download the model and go through the exercise. Private message me with your thoughts!

In 2004, I left Microsoft so Patty and I could homeschool our son Trevor. He was diagnosed with Autism Spectrum Disorder at age five, and we decided as he was entering seventh grade that he would need more help than what his public school could offer. I was his math and science teacher for two years until he re-entered public school in ninth grade. After my homeschooling stint, I decided to focus on writing and consulting, and later Patty and I starting a publishing business. From that point until now, I have regularly been asked if I’m “retired.” At first, I would respond with a strong “no” due to my opinion that retirees spend their days on the golf course or playing bridge. Over time, though, I recognized I had to come up with a better description of what I do as a profession. It’s not a choice of either the golf course or the 8-to-5 grind. For me, it’s something I call sustained lifestyle.

So, what’s sustained lifestyle? Here’s the definition, then we’ll unpack it:

Sustained lifestyle is when you have a high sense of achievement accompanied by a low degree of stress, making it something you can sustain for a long time.

First let’s talk about achievement. This is about doing something meaningful that accomplishes a desired result which gives you joy. It could be delivering a project on time, helping people in need, or coaching lesser experienced professionals. It’s about getting something done that matters to you and seeing the fruits of your labor.

Next is stress. This is the degree of mental, physical or emotional strain undertaken to achieve a desired result. Delivering a project on time with high-pressure executive meetings, project team infighting, and an unreasonable customer is much more taxing than one with cooperative execs, project team members, and customers. The end result is a completed project, but the execution was like pedaling uphill in tenth gear.

When stress and achievement are combined in the context of lifestyle, one of the four results are realized:

A frustration lifestyle is the result of high stress accompanied by low achievement. Think burning the midnight oil on projects that get cancelled last-minute or never used.

A boredom lifestyle is the result of low stress accompanied by low achievement. Think getting up every morning with nothing to do.

A burnout lifestyle is the result of high stress accompanied by high achievement. Think successive strategic projects with demanding customers, a dysfunctional team, and irrational management.

A sustained lifestyle is the result of low stress accompanied by high achievement. Think volunteering for a cause you’re passionate about on your work terms.

Now don’t get me wrong; I’m in no way saying that a sustained lifestyle means no stress. There are certainly things in life that crop up and cause great stress. However, a sustained lifestyle gives you margin to handle unexpected stress more effectively than if your stress bucket were already full.

Here are eight tips to create a sustained lifestyle that’s enjoyable and fulfilling for you:

1. Run to a vocation – Creating a sustained lifestyle entails having a post-career plan that you work to once you’ve left your job. The plan could be to discover your sustained lifestyle vocation or, if you already know what you want to do, how to make that sustained lifestyle a reality. Painting a picture in your head of what it will look like will help you get excited about giving it life.
2. Be clear on your decision criteria – Deciding on what your sustained lifestyle looks like means being very honest with yourself on your decision criteria. Is a continued income important or necessary? Will you need something that continues to feed your ego? Is the flexibility to say no to things important? No right or wrong answers on the criteria, but be deliberate about defining it. This Excel-based assessment tool will help you think about your criteria using nine crucial contentment elements. 
3. Make each day purposeful – I have a theme for each weekday that focuses on some aspect of my vocation; Monday is Amazon book ads day; Tuesday is article writing day (Yes, I’m writing this article on a Tuesday.); Wednesday is mentoring day, etc. While I may move things around based on schedules, I know what my core activities will be on each day of the week.
4. Agree on the guiding principles with your spouse/partner – Patty and I have several guiding principles on our sustained lifestyle, the most important being the freedom to do what we want from wherever we want. We enjoy travel and regularly do winter treks to warmer weather. We can continue publishing books and I can write regardless of where we are. Having an understanding between you and your spouse/partner about what is important and what you want to protect is crucial to a happy sustained lifestyle.
5. Have at least one goal you’re working toward – After my father-in-law sold his locksmith business, he took on other hobbies which kept him growing, most notably photography. Having goals not only keeps you learning, but also satisfies the need for a sense of accomplishment.
6. Be accountable – I am a member of a men’s business group that meets twice a month. Three of us want to drop some extra pounds, so we agreed that before each meeting we will share our current weight with each other. It’s amazing how much more I think about what I consume because I don’t want to report poor progress to my colleagues. Having accountability to someone else helps you focus on your goal and work harder to achieve it.  
7. Be mindful about what stresses you out – Keeping a wide distance between achievement and stress means being honest with yourself about what stresses you out and putting things in place to keep stress to a minimum. Know your stressors and keep them in check.
8. Create a comfortable space – I have a standup desk in our den with three monitors and a large screen TV on the wall. Every morning, after getting my first cup of coffee, I go to my workstation and use it throughout the day. It’s a very comfortable setup that I enjoy and don’t mind spending time at.

Whether you’re at retirement age, close to it, or merely thinking about it, keep the concept of a sustained lifestyle front and center. Think high achievement and low stress.