You don’t need to become a different Assistant to succeed in a new situation; you need a clearer map of the terrain you’re standing on, explains Kristine Valenzuela
If you’re lucky, you may have experienced an effortless connection with an executive. Lucy Brazier describes this bond as ‘when one of you breathes in, the other breathes out’. It’s almost a dream sequence: a masterful symphony of handoffs, unspoken cues, and quite literally reading each other’s minds. Even in moments of stress, work gets done in an effortless way and things just click into place.
Perhaps that’s a scenario you can only dream of. You may have been unlucky and worked with an executive that seemed nothing like that. An unfortunate scenario might involve awkward silence, micromanaging, irritation that’s visible but never discussed, or emotional outbursts over insignificant details. A worst-case scenario may involve all these things and resemble the toxic executives seen in the media. By far, the worst part of this type of connection is the emotional burden you carry onto the job. You know the feeling I’m talking about; the stress layers on top of itself day after day until you feel like nothing more than a cog in a machine.
Not surprisingly, the unfavorable situation tends to cause the most damage. The most experienced, esteemed Assistants can suddenly doubt themselves and wonder if they’ve lost their edge. Someone early in their career who experiences this may wonder if this line of work was the right choice. Both experiences are far more common than we talk about – and I can tell you it isn’t a failure of capability, even if the blame is placed on you.
The Situational Mismatch
Although this happens to people throughout their careers, it’s almost never defined. But the Executive Assistants (EAs) of the world deserve more, so I’m giving this a name: it’s a situational mismatch. This occurs anytime there’s a gap between an EA’s working style, instincts, and strengths and an executive’s decision-making style, communication patterns, risk tolerance, and expectations.
The best way to think of this is like a puzzle where there are two shapes that we think are meant to be combined, but instead, the shapes are from two different parts of the puzzle. When we look at it this way, we see this misalignment as contextual, not personal. The dynamic between an Executive Assistant and an executive must be looked at the same way, even though we almost always absorb it as a personal failing.
If it’s not us, then why does this happen? Executives operate with different information-processing speeds, control preferences, emotional transparency, and personalities. The biggest variable is that executives tend to have varying definitions of ‘support’. These are all factors that no one has control over. Sadly, the job of the Executive Assistant is usually to harmonize with their executive instantly with little acknowledgment of the (hefty) cognitive adaptation involved.
Volatile Environments
The speed at which business is changing is another reason you may find yourself in a situational mismatch. Leadership is a lot more complex these days, with frequent restructures, mergers, and reorganizations. To add to that, there could be fractional or interim leadership and matrixed reporting which are managed across global time zones. All of this complicates things to a high degree, and to be honest, I’m not sure most executives understand exactly how much these inputs affect the average employee. Yet part of the job of an Executive Assistant is to make every complexity seamless even if they’ve inherited executives mid-stream, without any shared history.
Easy, right? No. I’ve lived through these complexities more than once and getting onboarded with a new executive is a lot like being thrown into a pool and being told to swim. Rarely are we given the opportunity to slowly build a working relationship. The relationship is almost always forged under pressure, ambiguity, and urgency.
I’m pointing this out because all of this makes our role harder. It’s not because EAs are inferior, but because environments are more volatile.
When you look at it through this lens, this mismatch occurs because of many things outside of our control. However, the real tax lies in the fact that the Assistant usually bears most, if not all, of the burden.
We take this personally and fall into the following behaviors to compensate:
- Over-functioning
- People-pleasing
- Silence instead of curiosity
- Loss of confidence and voice
- Premature exits from roles (or the profession entirely)
If you’ve ever walked away from a role wondering what happened to the confident, capable Assistant you used to be, I encourage you to pause before you turn that question inward.
Effectiveness doesn’t disappear; it shifts depending on context.
Different executives create different conditions, and not all environments allow the same strengths to surface in the same way. Improving your situational intelligence gives you a way to understand those conditions without losing yourself inside them.
You don’t need to become a different Assistant to succeed in a new situation; you need a clearer map of the terrain you’re standing on. And once you have that, confidence isn’t something you manufacture. It’s something you reclaim.
I’m here to say absolutely none of this is your fault. When we don’t have language to fit a situation, we tend to turn everything into a character flaw. So, from now on, let’s keep our heads up and work smarter, not harder. Here are several frameworks to apply the next time you find yourself in a situational mismatch:
Tips for Correcting a Situational Mismatch
Scenario: When things with your executive seem off, you jump straight to working harder to prove yourself
Solution: Observe before you optimize; establish a short diagnostic period to understand how this executive operates individually and as a leader.
Scenario: You’re operating at a high level, but that seems to go unnoticed by your executive
Solution: Your skills and what your executive rewards may be at odds; ask yourself, what skills am I using here, and what skills does this executive reward?
Scenario: You land a new position and resort to operating as perfectly as possible
Solution: When forming a new partnership, you’re not becoming a different EA; instead, modify the skills you already have: adjust communication timing, level of detail, and framing of recommendations.
Scenario: You’ve done all the right things but still feel misaligned with your executive
Solution: Name the gap; come up with a talk track to neutrally surface misalignment with your executive; focus on work preferences and leave out any emotional descriptors.
Scenario: You start to doubt your skills and career choice when nothing you do clicks with your executive
Solution: Some dynamics are structurally incompatible and not meant to be, despite having all the right characteristics individually; just know that it’s not a failure on your part.
