Seven Secrets to Winning with Your Boss (Leading Up Part 4 of 4)

Seven Secrets to Winning with Your Boss (Leading Up Part 4 of 4) August 8, 2019

We All Want To Win

Here’s what I know about you: to win at work, you must relate effectively to your boss.

We can make a practical argument here. Perhaps no other single factor will better determine your advancement and well-being at work than your capacity to understand and influence your direct supervisor or supervisors. We can make a spiritual argument as well: the writers of scripture simultaneously taught their readers to 1) respect those in authority and 2) to understand that God is the ultimate authority with whom everyone will have to be accountable. So in deference to the final authority, God, you should dole out some respect to your boss, who’s a temporary authority in your life.

In the first post of this series, we’ve made an argument for facing the “well-being shaping reality” of bosses. Posts two and three were a deep dive into the four different motivational profiles of those who sit in the leadership chair. I advocate a “chess” approach to Leading Up. In chess, the pieces are each different and require tailored strategies. Relating to your boss is similar, there are at least four types of motivational patterns for bosses and thus four approaches to winning.

In this final post, I want to highlight seven general strategies based on character traits for influencing your boss or supervisor – no matter what their motivational profile. In “normal” cases, this will lead to respect, advancement, and influence. In terribly broken cases, these traits could lead to an exit on your part. Ultimate outcomes are beyond our direct control. It is fruitless to attempt to control your boss or to fix them. Instead, we settle into a way of being that aligns with these deep values.  We trust that things will work out at our current place of employment or at a future organization that appreciates these values. We begin with wisdom.


  1. Wisdom

A servant who deals wisely has the king’s favor, but his wrath falls on one who acts shamefully.(Proverbs 14:35)

Wisdom is knowing what to do and when to do it. Some might call it practical knowledge.  Being known as a person who discerns and follows the best path in relationship with colleagues, both in what you do and do not say is a path to influence.

Saying or doing things that in hindsight are embarrassing will ultimately result in declining fortunes. With bosses, it’s better to be quiet and invisible rather than outspoken and foolish.

How would you rate yourself on wisdom?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Truth

Righteous lips are the delight of a king, and he loves him who speaks what is right
(Proverbs 16:3)

Speaking the truth and pursuing what is fair and just; both of these behaviors are behind the words “righteous” and “right.” And these are the kinds of words leaders appreciate. Many hard-charging, type-A people have told me the single thing they value about me is that I tell them the truth. No flattery or pandering. Some leaders may not want to know the truth, and those are the types you don’t want to follow.

How would you rate yourself on truth-telling?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Sincerity

He who loves purity of heart, and whose speech is gracious, will have the king as his friend.(Proverbs 22:11)

To be pure in heart is to have sincere motives. Mature bosses are very good at sizing up people. They can quickly tell if you’re seriously committed or not; they can tell if you genuinely mean what you say or are trying to “fake it till you make it.” Why are you in your current role? What do you love about the work, the product or service, and the company? Answer those questions quickly and honestly, and you’re on your way to the kind of sincerity leaders love to find on their team.

How would you rate yourself on sincerity?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Tenacity:

With patience a ruler may be persuaded, and a soft tongue will break a bone. (Proverbs 25:15)

Today’s consumer culture trains us to get rapid results. Bosses and supervisors, especially those in large organizations, tend not to yield to suggestions for changes to be made. The secret in this situation is to think  “long game,” “distance run,” and give it time. Asking questions, presenting gentle and precise suggestions, actually have the power to bring about significant influence when brought with persistence, respect, and the proper timing.

Tenacity at work can be related to the idea of “time horizon,” an investment concept. Over what period do you expect to see a return? Have you given tenacity and savvy a reasonable amount of time to work?

How would you rate yourself on tenacity?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Grace Under Fire.

If the anger of the ruler rises against you, do not leave your place, for calmness will lay great offenses to rest. (Ecclesiastes 10:4)

So, what do you do when you’re called out in a meeting, falsely accused, or are required to report less-than-stellar results? How do you handle it if the boss yells at you in front of others? Do not cry, do not slam doors, and do not drop ultimatumsBreathe deeply, stay in your seat, and remain calm until the storm blows over.

If this becomes a pattern, address it privately with your boss. If it becomes a habit, a quiet exit, or even a report to HR are appropriate. Otherwise, take it.  Acknowledge responsibility for anything on your side of the desk.  Cultivating the qualities in this list will enable your emotional maturity and intelligence to eclipse that of many of your bosses. You will be the grown-up in the room. Usually, this will win them over.

How would you rate yourself on grace under fire?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Humility

Do not put yourself forward in the king’s presence or stand in the place of the great, for it is better to be told, “Come up here,” than to be put lower in the presence of a noble.    (Proverbs 25:6-7)

This “wisdom” is the complete opposite of the cutthroat business culture thriving in several major industries here in New York. Continually playing the game to get ahead is exhausting, and it is one of the reasons my clients come to me for executive coaching. The other risk is the that of overplaying one’s hand, grabbing a position of honor, power, or influence that has not been given. Constant posturing is a sure path to embarrassment and perhaps even corporate banishment.  Any boss who has people sense will see this for what it is, arrogance, and in most cases, this trait drives their opinion of you south.

Experienced bosses can also smell even just a whiff of flattery, quickly spotting the “player” across the room.  If they are building a respectful, engaging team culture, their esteem for you will sink. If they are building a “survival of the fittest,” shark culture, they will admire your spunk and pat you on the back. Their response to the grab-the-mic types, tells you what is valued in the workplace and gives you essential data from which to plan your next moves.

If you’re serious about being a Christian at work, fighting your way into the spotlight is antithetical to the way Jesus taught us, to the way that God promises to bless. He promised to bless the humble, to reward those who do their good in secret when only he is looking.

How would you rate yourself on humility?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


  1. Talent

Do you see a person man skillful in their work, they will stand before kings; they will not stand before obscure men. (Proverbs 22:29)

If you are not always working to look good in front of the boss, how can you get ahead?  By doing excellent work. Being great at what you do is the ticket to new levels of advancement, challenge, and responsibility.

Everybody can sing karaoke and record videos on their iPhone, but excellence is something for which we pay. We are spending more and more money to listen to the best artists and eat at the best restaurants. Your boss is paying for you to do your best. By continually growing in your capacity to deliver results with excellence and poise, you are giving him his money’s worth, and you are building the foundation for your future.

For many of us, being skillful at work involves both a technical dimension and a human dimension. There is a process, product, or service; we are expected to know well. We are also expected to communicate with and work well with others. Almost every job enables you to increase in either human or technical skill; many are learning labs for both.

At my firm, VOCA, we get up in the morning to help people understand the strongest talents, working with them so they can use their hard-wired abilities to win at work.

How would you rate yourself on employing your deepest talents at work?  Rate 5, if it is true of you always, rate 1 if it is never present in how you operate at work.

1          2          3          4          5


How About You?

1. What is your aggregate score?

  • 27 or above is a strong score. If your position is in a healthy organization in a strong line of business, you should be moving up.
  • 18-27 is a fair score. You are probably seeing moderate career growth, but are held back by one or two weak areas.
  • 9-18 is a moderate score. You are missing out on influence with your boss and opportunities for growth at work.
  • 9 or below is a low score. Your job is likely in jeopardy, especially if there is a contraction in your industry.

2. What is your weakest characteristic?  This factor  holds you back.  Work on this first. How will you change it over the next quarter? Then tackle your second weakest, etc.

3. Think about who the winners are at your office or company (those who have advanced or who are influencing those in management). Write down a few names. How many of them are characterized by the qualities listed above? If the winners match this list, what does that mean for your future? If the winners do not match this list if they are the opposite of the traits on this list, what does that mean for your future?

4. What is your single most important takeaway from this series on leading up? How will it change your way of acting and reacting on Monday?


Dr. Chip Roper writes Marketplace Faith from New York City, where he is Founder and President of the VOCA Center. Under Chip’s leadership, VOCA rescues clients like you from the forces that rob them of effectiveness and joy at work.    VOCA provides coaching, training, and consulting to individuals and organizations in NYC and beyond. Visit our faith-based website at and our market-facing menu of services at

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