.png)
Ever feel like you’ve developed a sixth sense when it comes to your executive? You know when they’re about to veto an idea, drag their feet on a decision, or (the classic) drop a last-minute request, just as you’re about to log off for the weekend?
❗Spoiler alert: That’s not magic. That’s instinct—your unofficial superpower, crafted through experience.
But here’s the thing, great instincts become unstoppable when paired with psychology and structured frameworks. Nail this combination, and you’ll not only sharpen your insights but also anticipate their needs, finesse your communication, and avoid the old game of “guess what mood the boss is in today.”
Curious? Good. Let’s break it all down.
Step 1: Start with Instinct – What’s Your Exec’s “Energy”?
Your executive’s energy is their unique working style, the way they operate under pressure, make decisions, and lead. Chances are, you’ve already got a solid radar for this.
Ask yourself
Are they results-driven (direct, competitive) or relationship-focused (empathetic, people-first)?
Do they thrive in chaos, or do they crave structured order like their morning coffee?
Are they open to change, or do they love the sweet, predictable rhythm of consistency?
Leadership research highlights a spectrum of styles that influence decision-making, team dynamics, and innovation.
Leadership Style Breakdown
Trait | Style | How It Impacts the Team |
🎯 Task vs. People | Task-oriented leaders focus on efficiency and results, while people-oriented leaders prioritise relationships. | People-first leaders create positive environments, while task-driven leaders optimise for output. |
☯️ Change vs. Stability | Transformational leaders drive innovation; transactional leaders maintain order. | Change-oriented execs embrace big shifts, while stability-focused ones favour consistency. |
🔏 Structure vs. Flexibility | Some leaders prefer strict processes, while others thrive in dynamic environments. | Rule-based leaders minimise risk; flexible ones adapt quickly to challenges. |
💡 Example: An EA I worked with supported an executive who thrived on structured environments, predictable workflows, and well-planned schedules, except for one glaring contradiction. Every Friday afternoon, without fail, they would drop urgent, last-minute requests that completely upended the EA’s carefully organised week.
At first, it seemed random, just part of the job. But instead of staying in reactive mode, she took a step back and analysed a couple months of these requests. A clear pattern emerged: her executive wasn’t deliberately being disruptive; rather, they were a reflective, big-picture thinker who used Friday afternoons to process everything from the week. Their last-minute asks weren’t impulsive, they were the result of end-of-week clarity when they finally had the mental space to focus on unresolved tasks.
Armed with this insight, she built a pre-emptive system. Every Wednesday morning, she’d send a short, structured check-in: "Before the end of the week, do you anticipate needing X, Y, or Z? I can get a head start to have it ready by Friday."
By shifting from reactive to proactive, she not only reduced last-minute fire drills but also aligned with her executive’s natural workflow, making both of their lives easier. The executive got what they needed before the stress kicked in, and she regained control over her schedule, without the Friday panic.
Understanding these leadership styles isn’t just theory, it’s something you already do instinctively. The next step? Turning that instinct into a strategic advantage with psychology.
Step 2: Apply Proven Psychological Frameworks
Your instincts are sharp. Now, let’s back them up with science.
1. The DISC Model – Power Moves & Environment Views
The DISC model (William Moulton Marston) helps decode how people perceive control over their environment. No psychobabble, just four categories based on behaviour patterns:
Style | Traits | How to Work With Them |
D – Dominance | Goal-oriented, decisive, hates fluff. | Get to the point. Focus on results. |
I – Inducement | Outgoing, big-picture thinker. | Bring energy, sell the vision. |
S – Submission | Reliable, people-first, cautious. | Offer reassurance, maintain consistency. |
C – Compliance | Detail-oriented, rule-focused. | Provide data, logic, and structured plans |
💡 How to use it:
Got a “D” on your hands? Get to the point. No fluff, just solutions.
Working with an “I”? Bring the enthusiasm and focus on big-picture dreams.
If they’re an “S,” lean into reassurance and predictability.
For a “C,” show up armed with data, plans, and bulletproof logic.
💡 Example: One CoS I know worked with a “D” exec who despised long explanations. Instead of sending detailed emails, they started structuring updates in bullet points with clear next steps. The result? Faster decisions, fewer back-and-forths.
2. The Big Five Personality Traits – What Drives Them?
This is one of psychology’s most researched tools, and it’ll give you the full 5-star rundown of your exec.
1️⃣ Openness: Are they all about innovation or prefer tried-and-tested methods?
2️⃣ Conscientiousness: Are they obsessed with structure or flexible with the process?
3️⃣ Extraversion: Do they thrive in meetings or need solo thinking time?
4️⃣ Agreeableness: Are they team-first or fiercely independent?
5️⃣ Neuroticism: Are they calm under pressure or prone to stress spirals?
💡 Pro Tip:
High Openness? Pitch fresh ideas.
High Conscientiousness? Provide detailed plans.
High Agreeableness? Highlight team collaboration.
Low Openness? Stick to proven strategies.
3. Cognitive Biases – Their Decision-Making Kryptonite
Even the sharpest executives are not immune to biases (spoiler: none of us are). Recognizing these biases can serve as a powerful tool, helping you predict decisions, or gently steer them toward better outcomes.
Understanding cognitive biases is essential for anticipating and shaping executive decision-making. Here are a few common biases executives often display:
Confirmation Bias
➡️ Searching for evidence that already aligns with their beliefs. ⬅️
Confirmation bias involves the tendency to search for, interpret, and remember information that confirms one's preconceptions. This bias can lead executives to favor data that supports their existing beliefs while disregarding contradictory evidence. It is a significant factor in strategic decision-making, as it can skew the evaluation of options and outcomes
Anchoring Bias
➡️ Heavily influenced by the first piece of data they hear. ⬅️
Anchoring bias occurs when individuals rely too heavily on the first piece of information they encounter (the "anchor") when making decisions. This can lead to skewed decision-making processes, as subsequent judgments are unduly influenced by the initial data point. In strategic management, anchoring can affect the assessment of risks and opportunities, leading to potentially suboptimal decisions
Recency Bias
➡️ Prioritising the latest info over what came before it. ⬅️
Recency bias is the tendency to prioritize the most recent information over older data. This can result in decisions that are overly influenced by recent events or trends, potentially overlooking long-term patterns or historical data that are equally important. In the context of performance management systems, recency bias can affect the evaluation of performance metrics and strategic outcomes
Sunk Cost Fallacy
➡️ Sticking with a bad choice because “we’ve come this far.” ⬅️
The sunk cost fallacy involves continuing a project or decision based on the cumulative prior investment (time, money, resources) rather than current and future benefits. This bias can lead executives to persist with failing strategies because of the resources already committed, rather than reassessing the situation objectively. It is a common pitfall in strategic decision-making, where past investments can cloud judgment
💡 How to use it:
Got a confirmation bias on your hands? Present alternative views before they settle.
Notice anchoring? Provide up-to-date info to shift outdated thinking.
Sunk cost vibes? Reframe losses as lessons, not failures.
Cognitive biases like confirmation bias, anchoring bias, recency bias, and the sunk cost fallacy can heavily influence executive decision-making, often leading to flawed outcomes. To make better strategic decisions and drive stronger organizational results, it is crucial to identify and address these biases. By understanding their impact, executives can implement more disciplined decision-making frameworks, ultimately enhancing the quality and effectiveness of their strategic choices.
Step 3: Speak Their Language & Influence Without Overreach
Now that you understand their energy, leadership style, and biases, it’s time to adapt your communication to maximise impact.
Become a Communication Chameleon
Adapt your style to fit theirs. Whether they’re quick, detail-driven, or big-picture thinkers, align your language so they “get” you.
🔹 Got a risk-taker? Lean into outcomes and big wins.
🔹 Got a cautious leader? Reassure them with guarantees, contingencies, and fail-safes.
🔹 Are they emotionally driven? Paint a picture that tugs at their decision-making heartstrings.
💡 Pro Move: Predict their choices before they make them.
A CoS I know recognised their CEO’s love-hate relationship with risk. Instead of pitching ideas randomly, they designed a three-slide system showing potential downsides with solutions. The CEO engaged more quickly, and buy-in improved dramatically.
Trust Your Gut, Back It with Science
Being a Chief of Staff or Executive Assistant isn’t just a job, it’s a craft. You are the bridge between vision and execution, the person who turns chaos into clarity, and the force that keeps everything moving forward.
You don’t only support leadership. You amplify it.
Your instincts are the brush 🖌️, and psychology-backed frameworks? The paint 🎨. Together, they create a masterpiece of collaboration, influence, and efficiency, a system where you anticipate, align, and adapt in ways that make everything work better.
The Takeaway
Great leaders don’t operate in isolation, they rely on people like you. People who see around corners, pre-empt problems, and create solutions before anyone even realises they’re needed.
You read the room, steer the conversation, and shape the strategy, all while making it look effortless. But it’s not effortless. It’s a skill. A superpower built on experience, intuition, and an understanding of human behaviour that most people never even realise they need.
The more you tune into your executive’s quirks, preferences, and decision-making patterns, the easier your role becomes. And the more indispensable you are.
Because let’s be honest, when you can predict their next move, influence decisions, and eliminate friction before it even appears, you’re not just supporting. You’re leading.
So go forth. Decode your executive. Shape the strategy. Own your impact.
Meg ✌️
PS - Want to Dive Deeper?
Check out these research papers on leadership psychology & decision-making biases:
📌Ekvall, G., & Arvonen, J. (1994). Leadership Profiles, Situation and Effectiveness. Creativity and Innovation Management, 3, 139-161. https://doi.org/10.1111/J.1467-8691.1994.TB00168.X
📌Alblooshi, M., Shamsuzzaman, M., & Haridy, S. (2020). The relationship between leadership styles and organisational innovation. European Journal of Innovation Management. https://doi.org/10.1108/ejim-11-2019-0339
📌 Cummings, G., Tate, K., Lee, S., Wong, C., Paananen, T., Micaroni, S., & Chatterjee, G. (2018). Leadership styles and outcome patterns for the nursing workforce and work environment: A systematic review.. International journal of nursing studies, 85, 19-60. https://doi.org/10.1016/j.ijnurstu.2018.04.016
📌Jia, X., Chen, J., Mei, L., & Wu, Q. (2018). How leadership matters in organizational innovation: a perspective of openness. Management Decision, 56, 6-25. https://doi.org/10.1108/MD-04-2017-0415
📌Specchia, M., Cozzolino, M., Carini, E., Pilla, A., Ricciardi, W., & Damiani, G. (2020). Leadership styles and job satisfaction. Results of a systematic review. European Journal of Public Health, 30. https://doi.org/10.1093/eurpub/ckaa165.165
📌Saleem, A., Dare, P., & Sang, G. (2022). Leadership styles and the process of organizational change during the pandemic. Frontiers in Psychology, 13. https://doi.org/10.3389/fpsyg.2022.920495
📌Gao, Z., Liu, Y., Zhao, C., Fu, Y., & Schriesheim, C. (2024). Winter is coming: An investigation of vigilant leadership, antecedents, and outcomes.. The Journal of applied psychology. https://doi.org/10.1037/apl0001175
📌Cummings, G., Macgregor, T., Davey, M., Lee, H., Wong, C., Lo, E., Muise, M., & Stafford, E. (2010). Leadership styles and outcome patterns for the nursing workforce and work environment: a systematic review.. International journal of nursing studies, 47 3, 363-85. https://doi.org/10.1016/j.ijnurstu.2009.08.006
📌Eagly, A., & Johnson, B. (1990). Gender and Leadership Style: A Meta-Analysis. Psychological Bulletin, 108, 233-256. https://doi.org/10.1037/0033-2909.108.2.233
📌Acciarini, C., Brunetta, F., & Boccardelli, P. (2020). Cognitive biases and decision-making strategies in times of change: a systematic literature review. Management Decision. https://doi.org/10.1108/md-07-2019-1006
📌Kahneman, D., Lovallo, D., & Sibony, O. (2011). Before you make that big decision.... Harvard business review, 89 6, 50-60, 137.
📌Hristov, I., Camilli, R., & Mechelli, A. (2022). Cognitive biases in implementing a performance management system: behavioral strategy for supporting managers’ decision-making processes. Management Research Review. https://doi.org/10.1108/mrr-11-2021-0777
📌Rovelli, K., & Allegretta, R. (2023). Framing decision-making: the role of executive functions, cognitive bias and reward. Neuropsychological Trends. https://doi.org/10.7358/neur-2023-033-rove
📌Gonçalves, C., & De Macedo Rocha, C. (2023). Cognitive biases in decision-making: applications on strategic management and rationality improvement. International Journal of Scientific Management and Tourism. https://doi.org/10.55905/ijsmtv9n3-023
📌Hall, K. (2007). Looking Beneath the Surface: The Impact of Psychology on Corporate Decision Making. Law & Psychology eJournal. https://doi.org/10.1108/03090550710816500
P.P.S.
Why do I even have the nerve to write this? Good question.
Honestly, I’m just someone who’s spent years working with incredible executives, navigating the chaos, and figuring things out along the way. I’ve had the privilege of being the right hand to some truly inspiring leaders, learning from every challenge, misstep, and breakthrough.
I also happen to have an MBA (if that counts for anything) and I’m currently studying organisational psychology, mostly because I find people and how we work together endlessly fascinating.
But really, none of that is the point. I’m just here to share what I’ve learned, in case it helps someone else. Take what’s useful, leave the rest, and know that you’re already doing far better than you probably give yourself credit for.
Now, go be brilliant. ✨
Comments