The CTO's Relationship Calculus

A Formula to Calculate Which Relationships Are Killing Your Effectiveness (and Which to Invest In)

In a world of endless meetings and constant demands, the technical prowess that propelled us into leadership roles isn't always enough to ensure our success. As CTOs, we're pulled in countless directions, by our teams who need guidance, by our C-suite peers who expect business insights, and by stakeholders who demand results. Yet many of us struggle with an invisible challenge that undermines our effectiveness: the inability to evaluate and optimize our professional relationships.

The Hidden Cost of People-Pleasing

Research reveals that technical leaders often display specific personality traits. Studies show that personality types such as ISTJ (Introverted, Sensing, Thinking, Judging) and ESTJ (Extraverted, Sensing, Thinking, Judging) are particularly common among engineers, with these types making up nearly half of engineering professionals according to some analyses.¹ These personality types tend to be logical, results-oriented, and detail-focused, qualities that serve technical work well.

However, these same analytical minds often struggle with people-pleasing tendencies. Unlike the methodical approach we take to technical problems, we frequently lack a framework for managing relationships, leading us to default to accommodation rather than strategic engagement.

As engineers, many of us were rewarded early in our careers for saying "yes" to challenges and taking on additional responsibilities. We built our reputations on being reliable problem-solvers. This behavior pattern, while valuable for individual contributors, becomes problematic when we step into leadership roles that require judicious allocation of our most precious resource: our time and attention.

In my coaching practice, I've seen this pattern repeatedly. CTOs who built their careers on technical problem-solving continue that pattern into leadership, personally diving into technical issues rather than empowering their teams, and agreeing to timeline requests that aren't realistic, all to maintain their reputation as the person who makes things happen.

This manifests as calendar chaos, days filled with meetings that don't move the needle, relationships that drain rather than energize, and a perpetual feeling of being spread too thin. We become reactive rather than strategic, and our effectiveness suffers.

The Relationship ROI Framework

To break this cycle, we need to apply the same analytical rigor to our relationships that we bring to our technical work. Just as we wouldn't invest engineering resources without considering the return, we shouldn't invest our time and energy in relationships without evaluating their value.

Why "Calculus"?

I use the term "Relationship Calculus" deliberately. In mathematics, calculus provides tools for analyzing systems that change continuously, studying rates of change, accumulation, and optimization. Similarly, our professional relationships are dynamic systems that require continuous analysis and adjustment.

As technically-minded leaders, we're well-equipped to apply this type of thinking. Just as we would calculate the efficiencies in our technical systems, we can apply a similar analytical framework to our relationships. The calculus involves variables (the people in our professional lives), functions (the nature of our interactions), derivatives (how these relationships change over time), and integrals (the cumulative impact of these relationships on our effectiveness).

The Relationship Value Formula

For those who appreciate mathematical frameworks, I've developed a formula to help quantify the value of professional relationships:

RV = (SV × SA) + (EV × EF) - (TC × TW)

Where:

• RV = Relationship Value

• SV = Strategic Value (1-10 scale: contribution to key objectives)

• SA = Strategic Alignment (0-1 scale: alignment with your priorities)

• EV = Emotional Value (1-10 scale: positive energy/support provided)

• EF = Emotional Frequency (0-1 scale: frequency of positive interactions)

• TC = Time Cost (hours per week invested)

• TW = Time Weight (value of your time, can use 1 for consistency)

This formula balances both strategic and emotional components of relationships against the time investment required. Relationships with high strategic and emotional value that consume reasonable time will have high overall value. Conversely, relationships that drain time without providing commensurate strategic or emotional returns will show a low or negative value.

The resulting number helps classify relationships:

• RV > 10: Strong Multipliers

• RV = 1-10: Mild Multipliers

• RV = -5 to 0: Maintainers

• RV < -5: Detractors

Examples From My Coaching Practice

Example 1: A Strong Multiplier. A CTO I coached evaluated his relationship with the company's CFO:

• Strategic Value (SV): 9 (CFO provided critical financial insights for technology investments)

• Strategic Alignment (SA): 0.9 (CFO was highly aligned with the CTO's vision)

• Emotional Value (EV): 7 (Interaction was energizing and positive)

• Emotional Frequency (EF): 0.8 (Most interactions were positive)

• Time Cost (TC): 2 hours per week

• Time Weight (TW): 1

RV = (9 × 0.9) + (7 × 0.8) - (2 × 1) = 8.1 + 5.6 - 2 = 11.7

With an RV of 11.7, this was clearly a Strong Multiplier relationship worth nurturing. The CTO started protecting their weekly meeting time as sacred and found ways to deepen the collaboration further.

Example 2: A Maintainer. Another CTO assessed her relationship with a project manager:

• Strategic Value (SV): 5 (Moderate contribution to objectives)

• Strategic Alignment (SA): 0.5 (Partially aligned with priorities)

• Emotional Value (EV): 4 (Neutral emotional impact)

• Emotional Frequency (EF): 0.6 (Sometimes positive)

• Time Cost (TC): 5 hours per week

• Time Weight (TW): 1

RV = (5 × 0.5) + (4 × 0.6) - (5 × 1) = 2.5 + 2.4 - 5 = -0.1

With an RV of -0.1, this was a Maintainer relationship. The CTO restructured their interaction pattern, moving from three hour-long meetings to one 30-minute session plus asynchronous updates, reducing the time cost while maintaining the necessary information flow.

Example 3: A Detractor. A third CTO evaluated his relationship with a demanding board member:

• Strategic Value (SV): 4 (Some useful strategic input)

• Strategic Alignment (SA): 0.3 (Often misaligned with priorities)

• Emotional Value (EV): 2 (Interactions typically draining)

• Emotional Frequency (EF): 0.2 (Rarely positive)

• Time Cost (TC): 8 hours per week

• Time Weight (TW): 1

RV = (4 × 0.3) + (2 × 0.2) - (8 × 1) = 1.2 + 0.4 - 8 = -6.4

With an RV of -6.4, this was clearly a Detractor relationship. The CTO worked with the CEO to restructure board communications, creating a briefing document that addressed the board members’ concerns while reducing direct interaction time to 2 hours monthly. This shifted the relationship from a severe detractor to a manageable maintainer.

While no formula can capture all the nuances of human relationships, this provides a starting point for a more objective assessment of your professional connections.

Value Exchange Assessment

For each key relationship in your professional sphere, consider what value you receive and what value you provide. Value can take many forms: information, influence, support, resources, connections, or learning opportunities. The goal isn't necessarily perfect balance, but awareness of the dynamics.

Many CTOs I've coached are surprised when they conduct this assessment. They often discover they're investing substantial time in relationships that provide minimal strategic value, while underinvesting in relationships that could significantly advance their most important initiatives.

Relationship Classification

Based on your assessment, classify relationships into three categories:

Multipliers are relationships that amplify your effectiveness. They provide insights, connections, or support that significantly enhance your ability to achieve your goals. They energize rather than drain you.

Maintainers are relationships that are neutral, neither significantly adding to nor detracting from your effectiveness. They might include routine stakeholders or team members who perform adequately without requiring intensive management.

Detractors are relationships that consume disproportionate energy relative to the value they provide. They might involve excessive conflict, drama, or management overhead.

This classification doesn’t diminish anyone’s importance but instead helps you understand your current dynamics and make smarter decisions about where your time and energy go.

Strategic Investment Planning

Once you've classified your relationships, develop a strategic approach to each category. Invest proactively in multipliers by scheduling regular check-ins and prioritizing these interactions. For maintainers, create efficient systems for managing these relationships, such as establishing clear expectations and boundaries. For detractors, implement stronger boundaries and consider whether the relationship can be transformed or needs to be ended.

Implementing the Relationship Calculus in Practice

Applying this framework requires both analysis and courage. Here are practical steps to implement the Relationship Calculus in your role as CTO:

Conduct a Relationship Audit

Set aside time to inventory your key professional relationships. Note the nature of each relationship, the time and energy it consumes, the value it provides, and the emotional impact it has on you. This analysis will reveal patterns you might not have recognized: recurring meetings that could be emails, team members who consistently energize or drain you, or stakeholders whose requests always seem to take precedence over your priorities.

In my coaching practice, I've seen CTOs discover that significant portions of their time are consumed by low-value interactions, often with individuals or groups representing only a small fraction of their strategic priorities. This awareness becomes the catalyst for restructuring their engagement model.

Create Clear Boundaries

Once you've identified your relationship classifications, establish appropriate boundaries for each category. For multipliers, ensure you're giving them adequate attention. For maintainers, create systems that allow you to fulfill your obligations efficiently. For detractors, limit availability, require structured communication, or delegate interactions when possible.

Develop Exit Strategies for Toxic Relationships

Some relationships cannot be salvaged or managed. They must be ended. This is particularly challenging for CTOs with people-pleasing tendencies. Develop approaches for transitioning responsibilities to others, having difficult conversations about changing relationship dynamics, and setting new expectations about your availability and engagement.

Build Your Relationship Portfolio Strategically

Just as you'd build a balanced investment portfolio, consciously cultivate a diverse set of professional relationships. The goal isn't to maximize the number of relationships but to curate a network that provides the support, challenge, and resources you need to succeed.

Overcoming the People-Pleaser Mindset

Implementing this framework requires confronting the people-pleasing tendencies that many technical leaders struggle with. Research on people-pleasing behaviors indicates they often stem from a fear of rejection, conflict avoidance, and a desire for external validation, all common challenges for technical professionals.

Recognize the Signs of People-Pleasing

Be alert to warning signs in your behavior, such as agreeing to commitments you later regret, feeling resentful about others' requests, or avoiding necessary conflict.

Many CTOs I work with notice they automatically say "yes" to requests, only to later recognize the pattern when explaining shifting priorities to their frustrated teams. Keeping a log of requests and your responses can help identify situations where your people-pleasing tendencies are strongest.

Reframe Your Thinking

Challenge the underlying beliefs that drive people-pleasing. Saying "no" doesn't make you a bad person or leader. Setting boundaries isn't selfish. It's necessary for effectiveness. Your value isn't determined by how much you accommodate others.

Practice Progressive Assertiveness

Start with smaller boundary-setting exercises and work up to more challenging situations. Begin by declining minor requests that don't align with your priorities, use "I'll get back to you" to create space for thoughtful decisions, and practice stating your needs directly.

A simple change that works for many CTOs is to replace immediate agreement with time-bounded consideration. Instead of saying "sure" when asked if you can look at something, say "I can look at that next Tuesday after 2 pm." This small shift forces requesters to consider whether their ask is important enough to schedule, and gives you control over when you address the request.

Measure Different Metrics

Shift your definition of success from "making everyone happy" to more strategic outcomes, such as team achievement of key objectives, personal work-life balance, and progress on strategic initiatives.

The Strategic Value of Saying No

For many CTOs, particularly those with people-pleasing tendencies, saying "no" feels like failure. Yet strategic declination is one of the most powerful tools in your leadership arsenal.

Consider what happens when you say "yes" to everything: your calendar fills with other people's priorities, strategic work gets pushed to evenings and weekends, and decision quality suffers due to attention fragmentation.

By contrast, strategic declination allows you to focus on truly important initiatives, develop team members by delegating appropriate tasks, reduce stress and prevent burnout, and model healthy boundaries for your organization.

The most transformative moment for many CTOs I've coached comes when they decline a non-essential commitment and, rather than experiencing the backlash they feared, receive appreciation for their prioritization. This experience teaches them that thoughtful, well-explained declination enhances rather than diminishes their reputation as a strategic leader.

Measuring the Impact of Relationship Optimization

How do you know if your relationship calculus is yielding results? In the short term, look for reduced meeting time, lower stress levels, and more time for strategic work. Medium-term indicators include improved team performance, better decision quality, and enhanced work-life balance. Long-term indicators encompass stronger organizational results, higher team retention, and greater personal job satisfaction.

Conclusion: From People-Pleasing to Strategic Relationship Management

The transition from people-pleasing to strategic relationship management represents a critical evolution in your leadership journey as a CTO. By applying analytical rigor to your relationships, using this relational calculus, you can optimize your most precious resource: time and attention.

This approach isn't about becoming cold or transactional. Rather, it's about being intentional with your relational investments so you can give your best to the people and initiatives that truly matter. The result is not just better professional outcomes, but a more sustainable and satisfying leadership experience.

The most successful CTOs aren't those who please everyone. They're those who make strategic choices about where to invest their limited relational capital. By understanding and applying the Relationship Calculus, you can join their ranks, transforming from a reactive people-pleaser to a strategic relationship investor.

What relationships in your professional sphere need reevaluation? Which are multiplying your effectiveness, and which are detracting from it? The answers to these questions may determine not just your effectiveness as a CTO, but your satisfaction and longevity in the role.

1. https://sites.tufts.edu/eeseniordesignhandbook/2014/personality-types/#:~:text=Analysis%20of%20Results,and%20are%20great%20problem%20solvers.