DEVELOPMENT
j truly thriving and which bits could do with some
alterations. We’ll come back to the latter shortly…
Check for alignment with your boss’s
true, long-term aspirations
If you’ve used the exercises above, you’ll have a
clear view of the direction you want to take your
career. That direction may include your current
executive; perhaps with some alterations to the
way you’re working together. Or perhaps thriving
for you means pastures new. Either way, you’re
likely to still have a boss going forwards and it’s
going to make a huge difference to your chances
of succeeding if their aspirations are sufficiently
aligned with yours.
If you’re hoping to stick with your current
boss, it’s worth mining your existing knowledge
and mapping out where you think they’re keen
to take their career over the coming years,
remembering to factor in the things you know
about their life outside work, too.
If you think you’re going to be changing
managers, choose your next leader wisely. Do
your due diligence when interviewing, ask good
questions that really get beneath the surface and
show you’re interested in the direction they want
to take over the coming years – not just in leading
their department or organisation, but in terms of
their own careers.
You’ll need to avoid them feeling like you’re
invading their privacy, of course, but a good boss
will value a genuine level of interest (and not just
self-interest) at the start of this hugely important
relationship.
2
Factor in your boss’s habits, needs and
mindsets
When looking to get the best from a relationship
– particularly a relationship under pressure or one
that’s facing some kind of change – it’s helpful to
think in terms of the habits, needs and mindsets
of the people on both sides of that relationship.
As an EA, you’re likely to be better than most
at empathising with your manager so you’ll
know your boss’s habits well – the good ones and
the not-so-good ones. You’ll understand their
immediate needs and how they sometimes drive
your boss to demonstrate some of those less-than-
helpful habits. You’ll have a view on their beliefs,
assumptions and expectations when it comes to a
range of topics, too.
So, when it comes to turning your aspirations
into reality, ask yourself the following:
w Habits: Which of my boss’s current habits will
help me to thrive going forwards? Which might
get in the way? What helpful and unhelpful habits
do we have in our relationship when it comes to
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56 Chief of Staff | April/May 2018
me achieving what I want to achieve?
Needs: What are my boss’s greatest needs? How
might those evolve over time? And what impact
might me pursuing my aspirations have on their
ability to get their needs met?
w Mindsets: What are my boss’s assumptions
when it comes to me and my role? How are they
expecting my own career to evolve over time?
What do they expect our relationship to look like
in three years’ time?
w
Have the conversation
You’ll no doubt have a lot of conversations
with your boss, but for most PAs those focus
on the day-to-day, the events and tasks of the
coming weeks and months.
Much rarer are conversations about the
broader, deeper and more future-focused things
in life – so, it’s time to talk to them about what
you really, really want. I’ve found the key to many
of these conversations is to get the right blend of
authenticity, responsibility and courage – three
qualities I summarise as ARC.
To put it into context:
w Be authentic by being open and honest, staying
true to your core values, treating each other as
equal human beings and being prepared to take a
long hard look at yourself.
w Be responsible by recognising that you may not
be able to have everything on your wish list (or
at least not right away), that your boss and the
people around you will have to get their needs
met if they’re going to help you meet yours, and
that you may need to adapt your own habits,
needs and mindsets to find a mutually beneficial
way forward.
w Be courageous by being bold enough to share
your aspirations, even when they might conflict
with existing agendas. And be brave enough to
discuss the habits, needs and mindsets that could
limit this relationship’s potential for enabling you
and your boss to thrive.
4
To summarise, thriving in this relationship –
and in your career as a whole – means working
out what it is that you really, really want. And
you’re more likely to thrive if your aspirations are
sufficiently aligned with your boss’s true, long-
term aspirations and if you can factor in (and
adapt to) their habits, needs and mindsets.
Finally, given the importance of healthy
dialogue in any relationship, thriving is going
to be all the more likely if you can have the
necessary conversations with your boss in a way
that is simultaneously authentic, responsible and
courageous. S
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