Compass Questions: A Simple Tool for Complex Workplace Decisions

When Marcus was offered a promotion to team lead, he felt torn. The role promised more pay and visibility, but also meant working more closely with a boss who often undermined his staff. He caught himself wondering:

“Will this step make me more of the leader I want to be, or less?”

That single question didn’t hand him an instant answer, but it gave him something more valuable: a compass he could return to whenever the decision felt overwhelming.

This is the power of a compass question—a guiding inquiry that helps you navigate complexity, stay aligned with your values, and make choices you won’t regret.

What Is a Compass Question?

A compass question isn’t designed to solve problems on the spot. Instead, it’s a directional tool—a way to check whether a choice, relationship, or opportunity at work is moving you closer to or farther from what matters most.

Where problem-solving questions are tactical (“How do I convince my boss to stop micromanaging?”), compass questions are value-based (“Am I growing in confidence here, or shrinking?”). They anchor you to the professional you want to be, not just the problem you want to solve.

When to Use Compass Questions

Compass questions are especially useful when:

• The signals are mixed. A job offer or new project is both exciting and concerning.

• Relationships are strained. You’re deciding whether to keep investing in a manager, coworker, or direct report.

• Your integrity feels tested. You’re under pressure to cut corners or compromise your values.

In short: whenever clarity is clouded by competing pressures, a compass question helps you find your bearings.

How to Create Your Own

A good compass question has three parts:

1. Anchor it to your values. What do you most want to embody at work—integrity, growth, balance, leadership?

2. Frame a contrast. Ask whether a choice builds or erodes those values.

3. Keep it simple. Make it short and memorable, so you can recall it under stress.

Examples:

• Does this role energize me, or does it drain me?

• Am I becoming a stronger leader here, or more defensive?

• Will saying yes move me closer to my long-term purpose, or just keep me busy?

Real-World Examples

The Difficult Boss
Alisha’s manager is more critical than supportive. Her compass question is: Does staying on this team help me grow in resilience, or is it undermining my confidence? After six months, she realizes the role is more corrosive than constructive and makes a move.

The Tempting Project
Jorge is offered a high-profile assignment with a grueling timeline. His compass question: Will this assignment bring me closer to balance, or throw me off course? That clarity helps him negotiate flexible hours before accepting.

The Team Conflict
Priya leads a divided team. Her compass question: Is my approach to this conflict making me the leader I want to be, or am I shrinking back? Each time tensions rise, the question nudges her toward fairness and courage—shifting both her behavior and the team culture.

Why Compass Questions Work

The workplace is full of ambiguity and competing demands. A compass question won’t make the road easy, but it ensures you stay oriented to your values. Over time, that means clearer decisions, stronger leadership, and greater trust in yourself.

If you’re facing a crossroads right now, try asking:

“Does this choice bring me closer to the professional I want to be, or farther away?”

It might not give you the final answer, but it will point you toward your true north.

Escalating: When the System Must Become Involved

A few years ago, I worked with an employee in a municipal government office—we’ll call her Lauren. She had been in her role for several years and was widely respected. Her department hired a new employee, Eric, who initially made a strong impression on their supervisor. He was attentive, deferential, and eager to please. He stayed late. He complimented the boss frequently. He positioned himself as deeply committed to the mission.

But with his peers, it was a different story.

He made comments that were subtly demeaning. He joked about coworkers’ competence. He made inappropriate remarks that carried sexist undertones, often delivered with plausible deniability. When someone objected, he laughed it off. “Just kidding.”

Lauren and others tried lower-risk interventions first. They avoided reinforcing the behavior. They redirected conversations. In one case, a colleague addressed a comment directly and told him it wasn’t appropriate.

The behavior continued.

Lauren found herself in a difficult position. Eric’s behavior was eroding psychological safety in the office. But his strong relationship with their supervisor made informal resolution unlikely to succeed.

She realized that if the situation was going to improve, she might need to escalate it.

Before taking action, she did something essential: she conducted research.

She reviewed the city’s HR policies. She learned what constituted inappropriate workplace conduct. She studied the reporting procedures. She paid particular attention to confidentiality provisions and protections against retaliation.

She also sought guidance from confidential resources.

She contacted the Employee Assistance Program (EAP), which provided a safe, confidential space to think through the situation. The counselor helped her clarify her observations, distinguish facts from interpretations, and understand her options.

She also reached out to the municipal Ombuds office. The Ombuds explained how complaints were handled, what confidentiality could and could not be guaranteed, and what protections existed for employees who raised concerns in good faith.

These conversations helped her move from uncertainty to clarity.

Only after gathering this information did she proceed with a formal report.

The process was not easy. It required courage. There was no guarantee of a comfortable outcome.

But her actions had an impact.

Others who had experienced similar behavior came forward. Patterns became visible that had previously remained fragmented and invisible. Leadership was able to intervene appropriately. The workplace became safer and more respectful.

Escalation is often misunderstood as an act of aggression or disloyalty. In reality, it is often an act of stewardship.

Workplaces depend on formal systems—HR departments, unions, ethics offices, Ombuds programs—to maintain fairness and accountability. These systems cannot function if people are unwilling to use them.

Escalation should generally follow thoughtful preparation. Key steps include:

• Documenting specific behaviors and their impact

• Reviewing organizational policies and reporting procedures

• Understanding what confidentiality can and cannot be guaranteed

• Learning what protections exist against retaliation

• Consulting confidential resources such as an EAP or Ombuds office

EAPs and Ombuds programs are especially valuable because they allow employees to explore options safely, without triggering formal action prematurely.

Escalation may feel risky. It may create anxiety. It may alter workplace dynamics.

But there are times when escalation is not only appropriate—it is a moral duty.

When harmful behavior persists despite good-faith efforts to address it informally, escalation becomes a way of protecting not only oneself, but others—and the integrity of the workplace itself.

Escalation is not the abandonment of relationship. It is the recognition that healthy relationships require healthy systems.

Taking Responsibility: The Fastest Way to Restore Trust

A line worker at a manufacturing plant I consulted with—we’ll call him Miguel—had a reputation for being highly skilled and dependable. He rarely made mistakes, and when he did, he fixed them quickly.

One morning, during a particularly busy shift, Miguel noticed that a machine downstream from his station had jammed. The operator at that station, Dana, was already under pressure to keep the line moving. Miguel believed the jam was related to how materials had been fed from his station—but instead of stopping the line immediately to investigate, he made a small adjustment and let production continue.

Later that day, the problem worsened. The line had to be stopped entirely. Dana and the supervisor spent over an hour diagnosing and clearing the issue. Production targets were missed.

Miguel realized that his earlier decision—to keep the line moving rather than stop and fully address the issue—had contributed to the larger disruption.

No one confronted him. No one accused him.

But the next morning, before the shift began, Miguel approached Dana.

He said, “Yesterday, when I saw that material wasn’t feeding cleanly from my station, I adjusted it and let the line keep running instead of stopping to fully check it. I can see now that this contributed to the jam at your station and the downtime that followed.”

He then made a commitment:

“Going forward, if I see something that might cause problems downstream, I’m going to stop the line and fully address it, even if it slows things down in the moment.”

Dana nodded. She hadn’t been sure whether he had recognized his role in the situation. Hearing him take responsibility changed how she saw him—not as someone who had caused a problem, but as someone she could trust.

A week later, Miguel followed up.

“I’ve been paying closer attention to feed alignment and stopping the line when needed. Have you noticed a difference? Is there anything else you’d like me to do differently?”

She told him she had noticed. The downstream station had been running more smoothly.

This is the power of taking responsibility proactively, without waiting to be confronted.

The most effective way to do this is to use the same “behavior plus impact” formula that is used when giving feedback to others—but applied to yourself.

Name the behavior clearly:

“Yesterday, I let material continue feeding even though I saw it wasn’t aligned properly.”

Name the impact:

“That contributed to the jam at your station and the downtime that followed.”

Then make a specific commitment:

“Going forward, I will stop the line immediately when I see a potential alignment issue.”

This clarity reassures others that the lesson has been learned and that change is underway.

Finally, check in later to confirm the repair:

“Have you noticed an improvement? Is there anything further I should adjust?”

This step completes the cycle. It transforms responsibility from a statement into a sustained behavioral shift.

Taking responsibility in this way strengthens not only the relationship, but the entire system. It signals professionalism, integrity, and shared ownership of results.

In healthy workplaces, trust is built not by avoiding mistakes, but by responding to them with honesty and accountability.

Asking for Feedback: The Intervention That Changes the Pattern

A senior leader I worked with came to me puzzled by a pattern he couldn’t quite explain. He was highly competent, deeply committed to his team, and widely respected. Yet one of his direct reports seemed increasingly withdrawn in meetings. She spoke less, deferred more often, and no longer brought forward ideas with the same energy she once had.

His initial interpretations were external. Perhaps she was disengaged. Perhaps she lacked confidence. Perhaps she was considering leaving.

To his credit, he chose a different intervention. He asked her for feedback.

He said, “I’ve noticed that our interactions have changed, and I want to make sure I’m not contributing to that in some way. Is there anything I’ve been doing that’s made it harder for you to do your best work?”

She hesitated at first. Then she told him something he hadn’t realized.

“In meetings,” she said, “you often respond very quickly when I present an idea. You point out potential problems right away. I know you’re trying to strengthen the idea, but in the moment it feels like it’s being shut down before it has room to breathe.”

He was surprised. From his perspective, he was being engaged and helpful. But he could see how his speed and intensity might feel discouraging.

He didn’t defend himself. He thanked her.

And then he did something essential: he made a visible change.

In the next meeting, when she presented an idea, he paused. He let the room sit with it. He asked a curious question instead of offering an immediate critique.

The shift was subtle, but unmistakable.

Over time, she began contributing more again. The pattern had changed—not because he had forced it, but because he had invited information and acted on it.

This is the critical second step of asking for feedback: you must demonstrate, however modestly, that you have taken it onboard.

Without this step, asking for feedback can feel performative. People conclude, consciously or unconsciously, that it wasn’t safe or useful to be honest. They become less likely to offer meaningful input in the future.

Even small adjustments signal seriousness. They show respect. They build trust.

One of the most effective ways to structure a feedback request is to use the “Start, Stop, Keep Doing” framework. You might say:

• “What’s one thing I should start doing that would make me more effective?”

• “What’s one thing I should stop doing that might be getting in the way?”

• “What’s one thing I should keep doing that’s helpful?”

This structure creates balance. It prevents the conversation from becoming either artificially polite or disproportionately critical. It gives the other person permission to offer constructive feedback while also recognizing your strengths.

Asking for feedback changes the emotional geometry of the relationship. Instead of positioning yourself as evaluator, you become a learner. Instead of defending your self-image, you expand it.

And when people see that their feedback leads to real change, they become more invested in your growth—and in the relationship itself.

Bonding Activities: When Connection Is the Intervention

This is one in a series of articles about the Relationship Course Correction Menu

Several years ago, a manager I was coaching found himself in a frustrating dynamic with a colleague in another department. Every interaction felt tense. Emails were terse. Meetings felt guarded. He believed she was being unnecessarily difficult, and he was beginning to interpret her behavior as a sign of disrespect.

His instinct was to address the issue directly—to give constructive feedback or to name the tension explicitly. But after studying the relationship more closely, he realized something important: they had never established any real human connection. Every interaction had been purely transactional.

So instead of confronting the problem directly, he chose a different intervention. He invited her to lunch.

Not just any lunch. He had noticed, in passing, that she was passionate about trail running. He asked if she’d be willing to join him for a walk on a local trail during lunch, framing it as an opportunity to get outside and take a break from the office.

She accepted.

During that walk, something shifted. They talked about running, about how she had gotten into it, about the mental clarity it gave her. He listened with genuine curiosity. They also talked about their early career experiences, their families, and the pressures they were each navigating.

Nothing about their specific work conflict was discussed.

But afterward, everything about their working relationship became easier.

Her emails became warmer. Meetings became more collaborative. When disagreements arose, they navigated them with greater ease and mutual respect. The underlying technical issues hadn’t disappeared—but the relational foundation had changed. They were no longer strangers. They were allies.

Bonding works because it strengthens the emotional substrate of the relationship. It increases goodwill, trust, and psychological safety. These qualities make all other interventions—requests, feedback, problem-solving—more likely to succeed.

However, bonding must come from a genuine place. People are remarkably sensitive to motive. If someone senses that an invitation is merely a tactic to manipulate them or “butter them up,” it has the opposite effect. It undermines trust.

Authentic bonding communicates something deeper: I see you as a person. I am interested in what matters to you.

One of the most effective ways to signal this is to invite someone into an activity you know they enjoy. When you do this, you demonstrate attunement. You show that you’ve been paying attention. You reveal that your interest is grounded in real observation, not strategy alone.

Bonding is not a workaround. It is not a trick.

It is an investment in the relationship itself.

And sometimes, strengthening the bond is the most powerful intervention available.

Expanding the Relationship Course Correction Menu

In 2023, I wrote a series of blog post on my "Relationship Course Correction Menu", a list of interventions you can choose from when you're trying to improve any relationship. The earlier ones in the list involve less risk, the later ones require you to put more chips on the table. They build on each other in the sense that the skills you learn in the earlier ones are building blocks in the later ones. While the main focus of my work is improving relationships in the workplace, these techniques work just as well with personal relationships as they do with professional ones. Below are the links to all the essays in this series. Here’s an index of those posts:

The Relationship Course Correction Menu

1. Practicing Serenity in Relationships

2. How to Study a Relationship

3. Holding and Mirroring: The Functions of Effective Listening

4. The Power of Positive Feedback

5. If Only I Had Asked ... Making Skillful Requests

6. Building Your Relationship with Constructive Feedback

7. Describing a Fork In the Road

8. Good to the Last Drop: When and How to End a Relationship

As I’ve worked with clients in immersive role plays that reflect the real situations they face in the workplace, program participants have surfaced other strategies that belong on this list. With that in mind, you can look forward to blog articles on:

• Bonding Activities – Strengthening the relationship by connecting with someone on a human level outside of the usual workplace setting.

• Asking for Feedback – Strengthening the relationship by inviting the other person’s perspective and demonstrating openness to personal change.

• Taking Responsibility – Strengthening the relationship by acknowledging your own behavior and its impact, and committing to doing things differently.

• Escalating – Protecting yourself and others by using formal organizational channels when direct efforts have not resolved the problem.

One of the most powerful impacts of my programs on participants is that they have more options on the menu for how they can ap

Quote of the Week

Live Webinar: Don't Be Afraid: Learn How to Conquer Your Fear

Friday, June 10, from 1:00 p.m. - 2:00 p.m., I’ll be hosting a Live Webinar called: ”Don’t Be Afraid: Learn How to Conquer Your Fear”. Below is the course description. Register here. I hope you can make it! If you’d like me to teach a similar session for your team, schedule a free consultation.

Picturing yourself in a serene natural setting reduces fear by sending a message of safety to your nervous system.

Don’t Be Afraid: Learn How to Conquer Your Fear

Learn practical techniques for reducing fear and rediscovering a sense of power.

Fear is a natural reaction Nature has given us to help us deal with stressful life and death situations. In today’s world, though, fear is often an overreaction that paralyzes us, and keeps us stuck.

Has anxiety about public speaking kept your ideas from having the impact they deserve? Do you avoid difficult conversations because you’re afraid you’ll permanently damage an important workplace relationship? Have you ever put off starting an important project because you’re worried it won’t be perfect? If so, it’s time to do something about your fear. This course will show you practical techniques for reducing fear, and rediscovering a sense of power, confidence, and agency, so that you can make a bigger and more positive impact in your work.

To Keep Your Best Talent During the Great Resignation, Focus on the Employee Value Proposition

A version of this article was initially published in NPC Connections, the Nonprofit Center of the Berkshires Quarterly Online Magazine.

A large non-profit, which shall remain nameless, decided that they had put enough COVID precautions in place, and it was time for employees to return to their offices.  Wanting to give employees the ability to make choices for their personal safety, they allowed employees to opt to do their meetings by Zoom.  As a result, a peculiar situation developed.  Employees were now forced to commute into their offices, but most went into their offices and closed their doors, having only minimal in person interactions with their colleagues.  The policy had created the worst of both worlds.  They had taken away the telecommuting option which had become an important benefit for staff, but reaped none of the benefits of in person interaction.  You can imagine the griping.  Employee engagement suffered, and along with it, the organization’s reputation as an employer.

Employers cannot afford to needlessly compromise employee engagement in today’s labor market, in which employees have many options and employers are competing fiercely for talent.  On the contrary, it’s imperative that employers do as much as they can to sweeten the deal and make it attractive for employees to stay and bring their best effort to their jobs.

Every day that your employees show up for work, they are voting with their feet.  They are making a statement that the deal they have with you is the best one that they can find.  They are saying that in some way their jobs represent a path to progress towards their larger life goals, for their careers, for their financial plans, for the part that work plays in the rest of their lives.  In other words, they have a sense, usually unspoken and not entirely conscious, of the deal they are getting with you as an employer, the balance of what they give to you and what you give to them.  I call this deal the “employment value proposition.”  

The employee value proposition has many dimensions, but at bottom it is an exchange of value similar to the purchases we make every day.

To retain your best talent, you need to understand what the employment value proposition of your staff is.  The more you value a particular employee, the more you need to know about what they are getting out of their jobs.  You also need to understand what factors may be making them sour on their employee experience.  Only then will you be able to make informed choices that can help you both to retain your best people and increase their engagement.  

There are a number of ways to find out what the employment value proposition is in the minds of your staff:

• Surveys.  These are usually administered in large organizations.  Surveys can provide valuable information about employee attitudes towards their total compensation, the workplace culture, opportunities for career development, and many other factors.  If you choose to administer a survey, there are two things to keep in mind.  First, surveying your employees is an implicit promise to them that you will make changes on the basis of what you learn.  If you’re not prepared to take on large scale projects to change your organization, it’s better not to survey in the first place.  Second, survey data will create more questions than answers.  You’re going to have to do interviews with focus groups to find our more about what the survey data is really telling you.  At best, survey data will tell you which topics you should focus on in your focus groups.

• Focus groups.  A structured interview with a representative group or groups across your organization can help to identify what is working well for your employees and what represent opportunities for improvement.  It’s important that employees trust that you genuinely care about what they say, and that there won’t be retaliation against them for providing constructive feedback.  It can be helpful to bring in an outside consultant to conduct these focus groups, to provide a guarantee of confidentiality.

• Stay Interviews.  Most people are familiar with exit interviews, which are used to understand the reasons why people are leaving and to get a better understanding of the dynamics in their immediate team.  But why wait until employees are leaving to do this important discovery work?  The more you value a particular employee, the more important it is for you to understand whether they are thinking of leaving, and why.  Just as important is finding out what is fueling an employee’s positive experience of working for you, so that you can continue to sculpt their experience in a way that makes them get even more from their experience.  More information about how to conduct stay interviews, along with the most important questions to ask, can be found here.

As a non-profit organization, you may not be able to give people the biggest raises, or provide people with glamorous corner offices.  Yet you can do something that many for profit organizations neglect to do: you can show your employees that you care.  By taking a genuine interest in their employee value proposition, and by striving to enhance it with the means at your disposal, you can do much to win the hearts and minds of the people that are the lifeblood of your organization. 

If you’d like to learn more about how to find out more about your top talent’s employee value proposition, and you’re not sure where to start, schedule a free consultation with me today!