Advice for Chiefs of Staff

TL:DR

• Plan your next step from day 1 and constantly work towards it. Be proactive and take ownership of your development. 

Over the last few years, Chief of Staff roles have exploded in popularity. 

Nowadays, more and more people from across VC, Banking and Consulting ask me about Chief of Staff roles and, as a firm, we’re seeing many of them successfully join corporates, investment funds and startups in this capacity. 

Overall, this is great. It can be a rewarding position that offers unrivalled access to senior management and insights into decision-making that would normally be reserved for people with many years of leadership experience. The Chief of Staff role can be a perfect springboard for a high-potential person to learn the ropes and build connections before taking on a general management role. 

Most people are now mindful that the Chief of Staff title is vague, often deliberately so. The title can mean a wide range of things and cover a huge scope of responsibilities that may otherwise fall to an Executive Assistant, Chief Commercial Officer, Chief Operations Officer, Chief Strategy Officer, Chief People Officer and so on for every other function. This sort of breadth and variety is usually well understood but it still pays to dig into the rationale for the creation of the Chief of Staff role and what the role is trying to solve for. 

The good advice that is commonly shared is “Do your due diligence on the person you will be supporting and why they are hiring for this role”. Seems obvious but make sure you aren’t working for a psycho and that the specific Chief of Staff role they are offering is a good match for you - i.e. is it admin-focused and is that a fit for you? Or is it all speech writing and research and do you want that? 

HOWEVER, something that people don’t consider enough is, what comes next?!

With the growth in Chief of Staff numbers in recent years, we are inevitably going to seeing a volume of these people reaching the 2-3 year mark and thinking about next steps in their career. Not all of them will be able to secure internal moves and promotions to general management positions, especially when the companies they joined may not be doing as well now as they were 2-3 years ago. Furthermore, a Chief of Staff is usually a supporting role. As such, when it comes to interviewing for your next role, it can be difficult to articulate and quantify your specific personal achievements as a Chief of Staff and therefore hard to exemplify your competencies and capabilities.

The Chief of Staff role will give you insight and access and help you build relationships with all key decision-makers and stakeholders in your organisation. However, if you can’t secure internal progression, a problem you are likely to encounter is that being a Chief of Staff in one company doesn’t necessarily set you up to run a P&L in another company. And if you move across to a Chief of Staff role in a new company, you will find you are starting from scratch in many of the aforementioned areas. 

My recommendation to Chiefs of Staff is, more than in any other role, you need to make sure you are decisively and proactively career-planning right from day one. 

Here are a few ways you can do this: 

• Volunteer to own projects as they come up. This way you can curate your individual achievements. Keep a record of projects you’ve scoped, planned and delivered, then aim to round out your experience of key business elements such as M&A, Fundraising, Investor Relations, Customer, Ops managing teams, etc. 
• Skill development. Think about your skills and capabilities on a monthly basis and note what you are better at than you were four weeks ago. Stay current with any technical skills by taking courses and attending events.
• Proactively build good relationships with HR and the key stakeholders for each department or business function. One of your most valuable attributes coming out of the Chief of Staff role will be your understanding of how to engage and influence the decision-makers across the company.
• Make no secret of the fact you want to progress from the Chief of Staff role. Don’t get two years in only to find the CEO is surprised you don’t want to stay in the role forever.