A Little Known, but Powerful Technique to Fast Track Your Career: Theo Epstein’s 20 Percent Rule

Lessons on Career Advancement from 43 Year-old Chicago Cubs President Theo Epstein

Chicago Cubs President Theo Epstein's 20 Percent Rule for Career AdvancementTheo Epstein (b.1973), president of baseball operations for the Chicago Cubs, has thus far had a stellar career as a sports executive.

As a freshman at Yale, Epstein was assertive enough to flaunt his role as a sports editor for the Yale student newspaper. After cold-contacting many professional sports teams to express interest in working for them, he grabbed the attention of a Yale alumnus at the Baltimore Orioles. This stroke of luck led to three consecutive summer-internships at the Orioles with increasing responsibilities.

After graduating from Yale with a degree in liberal arts, Epstein joined the Orioles full-time as a public relations assistant. His ingenuity caught the eye of Orioles President-CEO Larry Lucchino, who took Epstein under his wings. When Lucchino became team president of the San Diego Padres, he took Epstein and made him director of player development.

At Lucchino’s suggestion, Epstein also attended law school full-time whilst working 70 hour-weeks at the Padres. At that time, nobody on the small Padres’ management team had a law degree. By going to law school and getting a Juris Doctor degree, Epstein could help review players’ contracts. “Getting that seat at the table gave me the opportunity to be involved, and then my responsibilities grew from there,” he once recalled.

At age 28, Epstein moved again with Lucchino and joined the Boston Red Sox as general manager. In doing so, he became the youngest general manager in the history of Major League Baseball. Ten years later, in 2011, Epstein became president the Chicago Cubs.

At both the Red Sox and the Chicago Cubs, Epstein intelligently used complex statistical analytics to oversee the teams’ curse-breaking championships. In 2004, Epstein supervised the Red Sox’s sixth World Series Championship and ended their 86-year drought. And in 2016, when, under Epstein’s presidency, the Chicago Cubs finally won the World Series Championship 108 years after the previous time they did, their triumph ended the longest drought in professional sports.

Theo Epstein’s 20 Percent Rule: Undertake Your Boss’s Less Glamorous Responsibilities

In a recent interview (22:31-minute mark in this “The Axe Files” podcast) with the University of Chicago’s David Axelrod, Epstein revealed a career advancement technique that helped fast-track his career at the Orioles, the Padres and the Red Sox:

Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like … So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll both make them really happy, and improve their quality of life and their work experience. And also gain invaluable experience for yourself. If you do a good job with it, they’ll start to give you more and more responsibility.

Idea for Impact: Those Who Raise Their Hands Climb the Ladder Faster

Theo Epstein's 20 Percent Rule: Undertake Your Boss's Less Glamorous ResponsibilitiesHuman nature is such that everyone likes to do what he/she likes and not what should be done. If you can determine those aspects of your boss’ job that she hates and volunteer to help her with those responsibilities, you can expand your job’s horizons.

When you can seize such opportunities to raise your hand and sign up for tasks and responsibilities that aren’t particularly attractive, you not only learn by way of broader experiences and gain confidence, but also become more visible to management and situate yourself for a promotion. As I’ve written previously, before you can be seen as eligible for promotion, you should have demonstrated competence in doing a part of the new job you aspire to.

Seek out projects, prove that you’re eager and able to go the extra mile, and gain valuable face time with top executives.

Adapt to Your Boss’s Style: Cases from Andy Grove and Steve Ballmer’s Expectations in Meetings

Andy Grove’s Meeting Style at Intel

Andy Grove's Meeting Style at Intel Intel’s former Chairman and CEO Andy Grove (1936–2016) was known for his brash management style. He habitually resorted to fear as a management technique. In an effort to aggressively pursue the right answers, he devoted his focus to facts and data, as I wrote in my article on lessons from the Intel Pentium integer bug disaster.

In meetings, Grove expected his employees to be self-willed, clear-sighted, and obstinate. Grove wrote in his autobiography / management primer Only the Paranoid Survive (1996,) “Don’t sit on the sidelines waiting for senior people to make a decision so that you can later criticize them over a beer.”

With an “in-your-face” interpersonal style, Grove bellicosely challenged his interlocutors and called his meetings “constructive confrontations.” In contrast, his executives recalled them as “Hungarian inquisitions” in reference to his childhood in Hungary under Nazi and Communist regimes.

Recalling Grove’s technique for meetings, one executive said, “If you went into a meeting, you’d better have your data; you’d better have your opinion; and if you can’t defend your opinion, you have no right to be there.” In pursuit of accuracy and rationality, Grove would rip his employees’ ideas to shreds even while they were still on the first page of their carefully prepared presentations.

Steve Ballmer’s Meeting Style at Microsoft

Steve Ballmer's Meeting Style at Microsoft Another case in point is how Steve Ballmer conducted meetings. For most of his career as Microsoft’s CEO, Ballmer expected his employees to deliver a presentation he hadn’t seen before, take the “long and winding road” of discovery and exploration, and then arrive at the conclusion. This allowed Microsoft employees to expose Ballmer analytically to all their contemplations and postulations before steering him to their conclusions.

Years later, Ballmer reflected that this meeting style wasn’t efficient because, as a high-energy person, he couldn’t bear longwinded narratives and grew impatient for the conclusions. Ballmer changed his expectations of meetings and required employees to send him the presentation materials in advance. He would read them and directly venture into questions, asking for data and supporting evidence only if needed. This gave him greater focus in meetings.

Idea for Impact: Attune to Your Boss’s Communication Style

As I’ve discussed in previous articles, your ability to work well with others can mean the difference in whether your career progresses or stalls. To advance professionally, it’s particularly important that you have a good working relationship with your immediate supervisor.

Attune to Your Boss's Communication Style Bosses, like all people, differ greatly in their capacities and communication styles. You and your boss may be reasonably compatible or you may have entirely different communication preferences, temperaments, and styles. Regardless, you need to achieve a beneficial and cordial way of working with your boss.

Invest time and energy in understanding how your boss works, her ambitions and goals, her priorities, her strengths and weaknesses, the specificity she expects from your projects and decisions, her hot buttons, and her flash points.

Accommodate your boss’s work style. Discuss communication preferences and seek feedback. Be flexible. Ask questions to clarify what you don’t understand.

How to Give Project Updates to Top Management and Ask for Help [Two-Minute Mentor #7]

Project Updates to Top Management Top management is continually besieged with information and requests from across the organization. This makes it difficult to get their attention, especially when you need their intervention on a project.

To be effective in providing project updates to top management and seeking their help, it’s important to cut to the chase, simplify your message, and be brief.

  • Tell them where you are now in relation to the goals of your project. Don’t expect the big bosses to ferret up-to-date information about your project. Anticipate their questions and be ready with supporting data.
  • Tell them where you’re headed. Present your plans and tell them where you stand in relation to those plans.
  • Tell them how you’ll know when you’ve arrived at the goal.
  • Tell them how you plan to get where you’re going. Provide enough context to help the big bosses understand the challenges you face.
  • Tell them where you need their help and intervention. “Boss, we have conflicting customer specifications. I need your guidance about setting priorities.” Mention your recommendations and seek agreement. “Here is our recommended approach to the problem. Do you concur?”

Mail Bag: How to Cut Off A Boss Who Rambles [Managing Your Boss #4]

Mail Bag Kathy asked, “Every time I ask my boss a question about a process, I get a lecture instead of a quick yes-or-no answer or specific instructions. Is it necessary to listen patiently and let her finish her lengthy sermon, or can I cut her short and tell her that a brief answer is all I need?”

My short answer: Live with it.

Cut off a boss who rambles Interrupting and cutting short a boss in the middle of a conversation may be an impolite way of handling a harmless habit. Your boss may ramble on for a number of reasons—she may be uneasy, excited, or frustrated about the topic at hand. She may just be thinking aloud or stating some particulars about the subject matter. If she is uncertain about what she wants to say, she might blather about everything she can think of.

Here are some techniques that can help:

  • Try to meet your boss just before an appointment on her calendar, prior to lunch, or at the end of her day. This encourages her to stay within a set time limit—she’ll want to leave her desk or prepare for the next meeting.
  • Phrase your question or request in a way that suggests that you need only a brief answer. Open the conversation by saying, “I know you’re headed to Peter’s office, but may I have a minute of your time to talk about …”, “I’m up against a deadline but can’t proceed until our scheduled meeting. Can you please tell me quickly …,” or “I only have five minutes—can you explain how to ….”
  • If you must cut off a boss when she’s rambling, interrupt her only occasionally. Your boss’s rambling may simply be her attempt to clarify or reiterate some details. Politely say, “Would you please excuse me? I must get back to my desk for …” and state a verifiable reason. Next, if you have what you wanted from your boss, recap what you’ve heard from her by saying, “So, I will ….” Alternatively state, “I think this topic needs more time. What’s a good time to discuss this later today?”

Don’t be Friends with Your Employees

Don't be friends with your employees Be friendly with your employees, but don’t be friends with them.

To be effective, managers need to to be obliging when they can and tough when they must. The boss-employee relationship implies a power structure that makes managing friends quite challenging. It can be difficult to give objective performance feedback to your friends, convince them defer to your authority over them, or to decline requests for specific allowances without harming the friendship.

Few managers who’ve been promoted from within to manage their peers come out of the boss-employee relationship with their friendships intact.

If you decide to be friends with your employees, don’t do it at the expense of being a boss.

Telecommuting: Out of sight, Out of mind

Telecommuting: Out of sight = out of mind

Perils of telecommuting: Disconnectedness and diminished face time

For over four decades, employers have offered telecommuting and other flexible work arrangements to boost employee morale, promote work-life balance, and retain skilled workers. In spite of the ubiquity of electronic communication and accessibility to travel, a growing body of research has shown that it is significantly harder to build and maintain social relationships electronically than it is in person.

  • In the 1960s, Hewlett-Packard (HP) pioneered flexible work arrangements as part of its legendary “HP Way” culture. However, in year 2006, HP surprised employees and the HR industry by deciding to cutback telecommuting in one of its divisions to encourage employee interactivity, promote teamwork, and enable skilled workers to train the less-experienced employees.
  • A few years ago, an internal IBM study revealed that when teams went more than three days without a meeting, their happiness and productivity suffered. This promoted the “Making IBM Feel Small” initiative to promote face-to-face contact among its employees.

It’s important of show up and be “there”

Telecommuting - The importance of being 'there' Getting management to recognize you for your achievements and consider you for promotions and leadership positions has never been more challenging, especially at large companies. As I have mentioned in my previous articles, career success is no more about “who you know,” but rather about “who knows you” and what they know about you. Earning this recognition begins by showing up, “being there” and acting the part of a dedicated, enthusiastic employee.

Look, companies rarely promote employees who are not around to solve challenges and slug it out during tough times. For those of you who wish to graduate from individual contributor roles and get promoted to team-leader or management positions, telecommuting comes with a cost — reduced face time with your peers, management, and customers, and diminished opportunities to foster your management’s trust in your abilities. Therefore, telecommuting can be an impediment to climbing the corporate ladder.

Sucking up Isn’t a Requirement for Success

Be Resourceful Do not Suck Up

Consider the all-too-familiar boss’s pet employee at an office. He uses flattery, goes out of his way to help the boss, curries personal favors, and constantly tows the boss’s line no matter how unreasonable it is. He never corrects the boss when necessary. He either sugarcoats or withholds information that the boss would rather not hear. Over time, he has perfected the art of stroking his boss’s exaggerated sense of self-worth.

How about leaders who go overboard on their intention to exceed customer expectations and turn out to be “customer compelled?” They bend over backward to fulfill every whim and fancy of their customers to the likely peril of their own organization’s values and priorities.

Sucking up or brown-nosing is widespread approach to win a boss’s approval solely with one’s own self-interest in mind. Consider the consequences of sucking up:

  • An employee that sucks up to his boss loses the respect of his peers and employees. They assume positive discrimination and favoritism because of his ingratiatory behavior. The suck-up recursively promotes sucking up in his organization — he encourages others to establish themselves in his good graces.
  • Suck-ups quickly get into a pattern of slavishly reacting to every impulse of the boss. Without realizing, they become vulnerable to obligations to support their boss. Neither can they set limits on favors, nor do they stand up for themselves or their employees.

Sucking up is not a requirement for success

Be Resourceful, Don’t Suck Up

“One does not make the strengths of the boss productive by toadying to him. One does it by starting out with what is right and presenting it in a form which is accessible to the superior.”
* Peter Drucker, in The Effective Executive

Contrary to popular opinion, a vast majority of promotions are not handed out to employees who are most willing to suck up. Research and empirical evidence proves that employees who are honest, sincere, open, straightforward, and helpful earn management’s respect and attention over time. They move up fast because of their demonstrated ability to make the right choices. In addition, most people can innately distinguish the brown-nosers and differentiate genuine compliments from insincere flattery.

Do not suck up to the boss Do not get me wrong. There is enormous value in being helpful to the boss. After all, making yourself resourceful can go a long way in staying in the boss’s good graces. It can open professional opportunities and increase your access to new ideas, initiatives, and restricted information. However, there is an obvious boundary between doing favors and sucking up. Running an urgent errand when the boss is busy preparing for an important meeting or watching over his pet when he is travelling are well within reason. Compromising your values and priorities just to get on the boss’s side will not get you anywhere in the long term. Try these suggestions:

Ready for a Promotion?

Promotions Can be Stressful

Promotions Can be Stressful Last year, researchers at the University of Warwick found that the mental health of managers typically deteriorates after a job promotion.  Part of this anxiety is attributable to,

  1. the loss of the security of a familiar role and the established relationships around the role,
  2. perceived cognitive inadequacies concerning demands of the new position, and,
  3. the uncertainty of transition and the innate human resistance to change.

The greater part of this anxiety is a common career mistake. Often, professionals take up new responsibilities for which they are not entirely prepared. Even when management judged them as qualified for the new role, without thinking through a new role before accepting the promotion, these professionals unintentionally position themselves for stressful transitions, bitterness, or eventual failure.

When Is It Time to Move On?

Do not assume that you are ready for a promotion just because you possess the right academic background, you look the part, you have the right contacts within the company, or, you have impressed your management with your capability to develop a few good ideas and articulate them well.

Here are a few questions to reflect on and assess your chance of a successful promotion or a horizontal transition.

  • Are you enthusiastic about taking on a new role? Does the new role fit into your medium- and long-term career plans?
  • Have you been performing your present duties well enough to justify a promotion?
  • Do you have a successor in mind for your current role? Have you made yourself replaceable? Are you willing to entrust your current responsibilities to a successor without a significant interruption in pace of work?
  • Ready for Promotion When Is It Time to Move On Are you qualified or experienced enough to do no less than, say, 40% of the new role reasonably well?
  • Have you demonstrated eagerness to gain knowledge of the new responsibilities?
  • Are you familiar with the responsibilities, autonomy, challenges, opportunities, and deliverables of the new role? Do you know how to get things done in the new role? Do you know where to get help?
  • Are you proficient with the communication, networking and interpersonal skills needed to make it in the new role? Will you get along with your peers, subordinates, and management at the new role?
  • Are you at ease with the demands on the new role: time, travel, pressures, and challenges? Can your family (or other aspects of your personal life) support this transition?
  • Can you swallow your pride if you are rejected for the new role? Are you ready to seek honest feedback about how management values you, listen, and make yourself more promotable in the future?

The more questions you answer with a “Yes” to, the better your chances for a successful promotion. Reflect on the questions you answer with a “No” to. Create a growth plan, improve your professional profile, and, ask for feedback from management on what you can do deserve a promotion.

Be Proactive and Seek Feedback from Your Manager

Seeking Proactive Feedback from Your Manager

Feedback is a critical component of our work. We need to understand whether our performance aligns with what is expected of us. We need to know what we are doing well, what we need to change and how we could improve. We need help to discover opportunities to advance our careers.

One of the common grievances of professionals is that their managers rarely give them adequate feedback. These feelings are not totally unfounded. Managers tend to be busy and deliver feedback only during cursory performance reviews. And, instinctively, managers fear confrontation: they assume that their employees may respond to even the slightest criticism with anger, defensiveness and alienation. Employees, for their part, resent feedback because they dislike being criticized.

This article suggests what you can do to effectively secure feedback from your manager. I have shared this process with several professionals who have successfully adopted it to further develop relationships with their managers.

Soliciting Feedback

  • Set up regular meetings with your manager to seek feedback. Do not wait for the quarterly or annual performance reviews to solicit it.
  • Prepare and send an agenda to your manager at least one day prior to your meeting. Use the questions in the following section to guide your discussions and agenda. Tailor the questions to suit your unique projects and goals. Cover all the broader, important topics on a regular basis.
  • Assure your manager that her opinions and suggestions matter and that you will listen to and act on them. You need not necessarily agree with every assessment, but remain open—do not grow defensive or angry. If you must disagree, do so politely. Offer your opinions using phrases such as “Could it be because …,” “how about …,” or “perhaps, another way to look at this is ….”
  • Ask for specific examples. Take down notes. Conclude the meeting by thanking your manager. Affirm that you will develop and share with her a plan of action.
  • Review your notes from the meeting. Look for patterns in her comments and suggestions. In a day or two, follow up with your action plan.

Ten Topics to Ask to Solicit Feedback from Your Manager

Ten Questions to Ask to Solicit Feedback from Your Manager

  • “How am I doing on project or goal X? What can I do differently to be more effective?
  • “My most important projects or goals are X, Y and Z. Do you think I have the priorities right?
  • “Am I meeting your expectations in keeping you updated on my progress / project X? How can I organize information better to help you understand my projects and our achievements?
  • “What goals do you see for me on project X (or over the next N months?) How will you measure me against these goals?
  • “What strengths do I bring to your team? What personal skills will enable me to grow and contribute better?
  • “How do you see my career developing in this organization over the long-term? What suggestions do you have to prepare me for such opportunities?
  • “What steps do you suggest I take to broaden my exposure to our functional area and build my skills? What specific steps can I take to widen my perspective in our functional area? What key challenges will I face?
  • “What can I do to expand my role? May I assume any additional responsibilities?
  • “What are your goals for the immediate future? What are your team’s most important projects and initiatives? How can I best support your goals?
  • “How do you think our organization and customers will change in the future? What opportunities do you see? What challenges will we face? How will our roles evolve? How can we prepare? What is our management’s perspective on the future?”

Concluding Thoughts

This article suggests an informal and practical process to solicit feedback from your manager. By exercising initiative, asking the right questions and proactively soliciting feedback, you can recognize and adapt to your manager’s and the organization’s expectations of you and discover prospects for larger responsibilities and promotions.

Your manager will appreciate your eagerness to openly communicate, improve, adapt, and contribute further. She will be more forthcoming in her assessment of your work and more likely to offer suggestions for improvement.

By understanding your manager’s expectations and priorities, you can secure the support and resources you need to achieve your goals. Keeping your manager informed helps foster dependability and build a stronger, mutually beneficial working relationship that helps you, your manager and the organization.

Never Surprise Your Boss [Managing Your Boss #2]

Managing your boss: never surprise your boss

Bosses Dislike Surprises–Positive or Negative

The world of work is awash with relentless changes, troubles and crises. In the midst of these uncertainties, your boss does not need surprises from you or any of her employees.

Bear in mind that your boss’s output is the aggregate of the outputs of all the members of her organization. She must be in complete control of her goals and be able to answer her boss’s questions about the status of her organization’s projects and progress made on the latest crises. Consequently, she does not expect to be blindsided by good or bad news on your projects. She needs to know the status of each of your significant projects, and the challenges and opportunities therein.

Keep Your Boss in Line

Never surprise your boss: Keep your boss in line A surprise is simply the difference between a previously-identified goal of a project and its apparent result. Give your boss a heads-up: have a conversation with her about forthcoming opportunities or mounting problems as soon as you perceive these variations in the output of your work.

Suit your boss’s preferred style of communication. If she is organized and detail-oriented, she may prefer comprehensive written reports itemizing the status of your projects, financial expenditures, and, performance against set goals and budgets. In contrast, if she is informal and perceptive, she may just need you to summarize the status of your projects in an email each week.

Pre-wire Your Boss Prior to Meetings

In meetings that include your boss, her boss, peers or customers, never introduce a contentious topic or discuss positive or negative details of your project without preparing your boss ahead of the meeting.

Make it a habit to meet with you boss prior to such meetings, show her drafts of your presentations and seek her comments and inputs. By ‘pre-wiring,’ or, discussing your findings and recommendations with key decision-makers ahead of a group presentation, you ensure their support for your conclusions and avoid surprise reactions or disagreements. See my earlier ‘Ideas for Impact’article for details on the technique of pre-wiring.

Be the First to Let Your Boss Know

As a rule of thumb, your boss should first learn about any surprise from you–not from her peer, her boss, customer or consultant. Recognize that, occasionally, you may not have discussed certain facts or figures with your boss solely because these details appeared irrelevant or unimportant to you. However, others may be experienced enough to foresee the consequences and, much to your chagrin, bring up the details with your boss. If your boss asks, “Carrie from accounting told me … why you didn’t tell me that?” acknowledge that you did not foresee the consequences. Learn from your lapses and discover how you could read such trends.

Managing your boss: Clarify mutual expectations early and often

Clarify Mutual Expectations Early and Often

If you see a need to reassess your goals and priorities on a project, bring it to the attention of your boss. Involve her in evaluating the challenges so that she feels just as accountable in redefining your common goals and priorities. Be prepared to clarify your thoughts and offer alternative solutions.

Realize that It’s a Matter of Trust

The relationship between you and your boss is a sensitive one–one that hinges on mutual cooperation, credibility and trust. Trust is a virtue that depends on the predictability of your behavior, honesty and dependability. If you surprise the boss repeatedly without forewarning, she may begin to mistrust you.

Concluding Thoughts

Your boss is important to you because she is the primary source of approval of your work. And, the relationship with your boss is a critical aspect of a favorable work atmosphere and your job satisfaction.

Success in building a relationship with your boss does not come easily. It begins with recognizing that this relationship hinges on open communication, cooperation, and credibility. The onus is on you to effectively manage this key relationship and achieve the best results for yourself, your boss and the organization.

Never keep your boss in the dark.