The Unique Challenges of Those Who Lead from the Middle
The middle is messy, full of contradictions and opposing agendas, and couldn’t be more critical for a company’s success.
And it’s you. Those who lead from the messy middle work in spots higher or lower in the organization, from Vice Presidents, General Managers, and Directors to Sales, Marketing, and Design Managers, and many more. They have a boss and are a boss, at any level. It’s anyone who has to lead up, down, and across an organization.
Whether you lead from the upper middle, mid‐middle, or way lower middle, if you have a boss and are a boss, if you lead up, down, and across an organization, take pride in your career‐making position. And know the best realize that being in a position in the middle doesn’t mean being stuck in the middle.
It means a chance to lead.
Leading Your Boss
Anyone who has ever had a boss knows that effectively influencing and interacting with said boss can be tricky and even angst inducing. Those who do it best realize that it’s not just one of the many relationships you must manage while leading from the middle, it’s the opportunity for a full‐on partnership, one vital for business success and that’s two times more critical for your career success than any other relationship, according to a McKinsey study.
Being held in high regard by your boss is one of the most powerful forms of influence and visibility you can wield. Not to mention that if you want to be considered good at managing people (which most of us do), people includes your boss.
Step 1: Nature Before Nurture
First and foremost, before you can nurture anything, it’s important to understand and embrace the fundamental nature of an effective boss and subordinate relationship. That is, it’s interdependence between two imperfect human beings.
Full stop.
Many employees struggle with their boss because they gloss over this truth. You need your boss, and they need you. And you’re both imperfect human beings.
Often frustrated employees reach the conclusion that they don’t need their boss, that the boss is just an impediment to success. Or they hammer their boss for their mistakes and flaws, labeling them in an unrecoverable way. If you don’t start by embracing the nature of the boss–subordinate relationship, the ideas of interdependence and fallibility, you can’t begin to nurture anything. Not only will you never reach true partnership with your boss, your basic relationship is doomed to fail.
Step 2: Understand the Asks
The problem lies in the assumptions we make and the lack of thoroughness on this front. Bosses rarely spell out exactly what they expect from the subordinate, and the subordinate too often falls short of fully comprehending.
To close the comprehension gap, ask the right questions of your boss, the ones that tease out the nuances of what they’re really expecting (and that help them better articulate it). Those questions are the ones that follow; specifically, nine of them. Ask your boss these questions even if you think you have a good handle on what’s expected of you.
1. “What does good performance look like? Great performance?”
2. “Let’s assume I’ll get great results—what behaviors do you want/not want to see as I achieve those results?”
3. “What business metrics/goals are the most important to you and why?”
4. “These are my top priorities—are they consistent with yours?”
5. “This is how I’m spending my time—does it feel like it’s supporting what’s most important?”
6. “What measures does your boss most frequently discuss with you?”
7. “What specifically will get you promoted?”
8. “What should I stop, start, and continue doing to better succeed?”
9. “Think of the most effective employee you’ve ever had working for you. What made them so effective?”
Step 3: Style Awareness
So many potential boss–subordinate partnerships never come close to fruition because the subordinate never took the time to understand the boss’s style, and to then adapt to it. You might not like adjusting your style to accommodate your boss’s, but it’s the lowest hanging fruit there is for achieving an effective partnership.
The power of this step comes from acknowledging and acting on the six key aspects of style that follow.
- Information Receipt and Retention
Since a fair amount of the boss–subordinate relationship is about exchanging information, it’s important to understand your boss’s style preferences on this front and to accommodate.
2. Decision‐Making
Knowing how your boss likes to make decisions makes you more effective in influencing what they ultimately decide. Do they like to “stew and chew” or decide quickly? How much information, of what kind, do they need before they’ll decide? Do they prefer consensus or just want to gather the information from different parties and make the final call?
3. Conflict
Does your boss like conflict or tend to avoid it? Do they go guns blazing into an argument or prefer a subtler approach to influencing? Do they prefer disagreement behind closed doors versus out in the open? If you know your boss likes conflict, you can help them be ready for “battle” by arming them with convincing data and arguments. That’s influence.
4. Formality
Does your boss like a lot of structure or to adhere to strict processes? Are they more formal in style or informal? Differences in styles here can create unintended impressions on performance.
5. Task versus People Orientation
As with so much in the middle, it’s about striving for a balance (one your boss can live with), that is, knowing when too much people focus is too much or knowing when it’s time to “get down to business” with your boss. Spending exorbitant amounts of time (in your boss’s eyes) discussing people matters can lead to unfair and unhelpful impressions about you being too “soft” or distracted from running the business effectively (as misguided as that may sound). On the other hand, being all business all the time can make you seem uncaring and lacking in emotional intelligence.
6. Behavioral
This is about knowing the behavioral traits that make your boss most comfortable (or uncomfortable) in the working relationship; what annoys them or creates bonds. Strong partnerships are more likely when both sides pay respect to the other’s personality trait preferences. And it should start with you. This isn’t about being a fake version of you, but simply paying attention to what works with your boss (or not) and making slight adjustments in your approach.
Step 4: Get Personal
If you can get away with getting personal earlier, great. It’s ultimately more important that you just make the effort to do so because a personal relationship forms the strongest roots of an effective and rewarding boss–subordinate partnership.
So how to get personal without overstepping? Have an agenda for learning about them, and work it over time, slowly getting them to share more and doing the same in return to build rapport. Reward their confidence with absolute discretion.
But do have a plan. Here are some things to seek to understand about them:
Understand their pressures, aspirations, hopes, and fears.
Understand what matters most to them in their life.
Ask what they like most about their workday and least about it.
Find out what they worry about most and what makes them the most uncomfortable.
Learn what motivates/energizes them, and what drains their energy.
Find out what they feel are their superpowers (greatest strengths), weaknesses or blind spots, regrets, and biggest accomplishments.
Discover their pet peeves and hot buttons.
The key is to make true connections versus trying to schmooze.
Step 5: Your House in Order
To manage up well, you have to be managing yourself well. That is, you must ensure you have your house, the basics of your job, in order. Otherwise your boss will be too distracted that you don’t have a firm grip on your core job to engage in anything else. Here are the five gut‐check, do I have my act together questions that discern if you’re set up to manage up.
1. Are you delivering the results expected of you?
2. Do you know your business, inside and out?
3. Have you asked for what you need?
4. Are you organized and prepared for interactions with your boss?
5. Are you bringing the attitude you want reciprocated?
Step 6: Purposeful Support
The support you offer should be intentional about the why and how to make your spirit of servitude more meaningful. It’s not about impressing your boss (although that’s certainly a great side effect), it’s about performing well in your duty to support your boss. To do so, know that there are six core areas your boss most values your support on and that most directly lead to a spirit of true partnership.
1. Information
2. Capacity
3. Decision‐Making
4. Problem‐Solving
5. Advocate
6. In Process
Partnerships with your boss blossom not only from what you provide support on, but how you provide it. In the process of supporting your boss, be mindful of these things in particular:
Treat your boss’s time as if it were your own. Selectively use their time (and resources) and be super‐efficient when you do. It’s one of the most basic forms of respect you can show.
Admit mistakes quickly and avoid unwanted surprises. Bury neither of these, no matter how painful. It feeds trust.
Ensure your opinion is heard but don’t overstep your bounds or try to upstage your boss. It erodes trust.
Be proactive and take initiative. Who doesn’t love someone who does?
Be a constant source of positive energy. Who doesn’t love someone who is?
Leading Those Who Report to You
Sure, as someone leading from the middle you get automatic influence over those who report to you because of your position power. But it’s personal power well‐wielded that separates the very best at effectively managing downward. The best at this know it’s about relationships, not reporting lines. Their efforts yield commitment versus compliance. They know it’s about being a facilitator, not a fixer, and that it’s about helping others improve, not proving their own depth of knowledge.
All of that will be you after reading and putting into play this play‐packed book. You’ll learn how to become a once‐in‐a‐career coach to your employees, how to have great coaching conversations, how to pinpoint their opportunity areas, how to give transformative feedback, and how to teach them in teachable moments.