Chynna Clayton, Michelle Obama’s former assistant, on finding success

Ever wondered how public figures and prominent business leaders make their work seem so effortless? They have a secret: their assistants.

Chynna Clayton, who held one of the most prominent assistant roles in existence: Special Assistant to the First Lady of the United States. During the Obama presidency, Chynna was Special Assistant and Director of Travel to Michelle Obama. 

We spoke to Chynna about her experiences at the White House, her career advice for aspiring assistants and her upcoming workshops for administration professionals. 

Eden Scott: Hi Chynna. What, in your opinion, makes ‘Assistant’ such an important role?

Chynna Clayton: The value of an assistant’s role is often underestimated. Our positions are multifaceted - yes, they involve planning and logistics, but they also require emotional intelligence, problem-solving and creativity. When you have good assistants within your organisation, you can be confident that tasks will get done and that they’ll be delivered correctly.

Assistants - be they personal, executive or special assistants - anticipate challenges and requirements before they’re even asked to. When I worked for Mrs Obama, I would consider everything from an event’s delegate list to the weather forecast. Good assistants are always prepared, removing roadblocks for leaders to do their jobs well.

ES: How can assistants progress their careers?

CC: Firstly, assistants should recognise that there is room for progression within their profession. All too often, ‘Assistant’ is seen as an entry level position without need for relevant qualifications and training. But we’re not ‘just assistants’ - we’re delivering a valuable service, and we need to refine our skills to do that effectively. 

I would recommend perfecting skills like anticipation, preparedness and communication. As assistants, our job is to make sure that our employers can perform well in their roles. We’re there to unburden them so that they can focus on only the essential tasks. If your boss is due to attend an event, for example, you should have all the information they need to hand - delegate list, attire, weather forecast - think about all the little details so that they don’t have to. 

Composure is also an essential quality for any assistants that want to progress. Composure is contagious. If you meet challenges with a sense of calm, you’ll instil the room with calmness. Leaders often look to their assistants for reassurance - so panicking is the worst thing you can do. Being composed means placing your emotions to one side and focussing on the steps you can take to remedy a challenging situation.

ES: Are those skills that can be taught, or are they qualities that people either have or don’t have?

CC: You might think that good assistants are all left-brained, type A personalities. That’s simply not true. At the White House, the assistants and administrative teams have a range of creative and logistical skills. 

So, I’d argue that while being organised and calm under pressure are essential to the role of assistant, they’re skills that can be acquired and perfected over time. 

ES: Did you ever get ‘stage fright’ during your time with the former FLOTUS?

CC: Of course! I was a baby when I started working with Mrs Obama - I joined the White House staff at 22 years old. When you see the President or the First Lady delivering a speech, talking to kids, visiting a disaster site or even going on a family bike ride, there are dozens of details that have been intricately planned in the background to make sure things go smoothly.

That’s a lot to take care of, so naturally, I often felt daunted. But  I think my willingness to learn from others helped to combat my fears. 

Early on in my role, I needed to figure out how to transport over 3,000 families from one event to the next when the number of buses we were originally promised dropped to half.

I started to feel like a failure and a poor representation of the First Lady’s Office. But, after talking to some more senior teammates, I was reassured that events beyond my control are not a reflection of me. This perspective made me realise that things do go wrong - as long as you’re owning your mistakes and learning from them, you’re on the right track.

ES: Yours is an exceptional career path - how can others replicate your success?

CC: I’ve been able to do some really amazing things in my life because I was willing to explore what was on the other side of my familiar. We tend to avoid the unfamiliar, but I’m a firm believer that new experiences make us stronger. To assistants progressing in their careers, I’d say, take the opportunities that come your way, even if they set your heart racing - there’s so much more waiting for you on the other side of that anxious feeling.

I’d also recommend finding yourself a good mentor. My mom prepared me for life’s obstacles and Mrs Obama was there to guide me while I was navigating them - they both helped me shift my mindset and recognise the value I bring to the table. When you are the ‘only’ in a lot of space - the only woman, the only person of colour, the only person your age - it’s easy to feel like you don't belong. My mentors helped me realise that there’s no room I don’t belong in - I’m as deserving as anyone else. Find yourself a mentor that makes you feel like that, and in turn, mentor someone whose confidence you can help to build.

What can attendees expect from your upcoming UK workshops?

I’m looking forward to sharing my experiences with other assistants. I hope they leave the workshops feeling empowered to progress in their careers. 

Assistants and administrators rarely get the chance to reflect on their career progression or receive career training - the workshops are designed to help PAs, EAs and administrators to grow confidence so that they can enhance the skills they need to perform to their full potential. 

You can catch Chynna at a series of EA/PA Excellence Workshops hosted by Own Your Success on Jun 27, Sep 20 and Nov 16.