Training a high-level assistant for long-term collaboration requires a strategic and thoughtful approach. A skilled assistant can help you stay organized, manage tasks efficiently and enable you to focus on strategic decision-making. However, training an assistant to work closely with you in the long term requires more than just assigning tasks and providing instructions.
Here, 16 Forbes Human Resources Council members share the key strategies that pave the way for a successful and enduring partnership with assistants. Whether you’re a business executive, an entrepreneur or a team leader, these expert tips will help you build a strong foundation for a harmonious and fruitful collaboration with your high-level assistant in the long run.
1. Introduce Your Assistant To Everyone
Introduce the assistant to everyone you can—inside and outside of the company. Often an executive’s time is spent simply connecting the right people to get things done. The assistant’s ability to connect people, communicate key messages and understand the impact of decisions on others can be critical components to success. – Kari Durham, Skyworks Solutions, Inc.
2. Express Your Interest In Their Success
Assist them! Communicate clearly how you are there to make them successful. – Dinesh Sheth, Green Circle Life
3. Share Your ‘Why’
It’s an essential step in creating a partnership. If your assistant can understand your objectives, it is easier for them to exercise creativity and flexibility in delivering service and solutions. – Megan Barbier, Boomi
4. Train Your Assistant To Think Like You
Work with the person to ensure they understand your way of thinking. The best assistants stay one step ahead and can easily work with others in a way that conveys “What would [insert your name]
do or say?” Training an assistant to consistently get this right ensures a solid long-term relationship. – Christina Hobbs, Force Scaling
5. Overshare When Training
It’s easy to feel like you are giving them too much information, that you are taking advantage or overdoing it by training assistants on absolutely everything you can think of. “Oversharing” is a good thing in this case. The more your assistant knows about you and your needs, wants, preferences, opinions and dislikes, the easier they can assist you and the more likely you’ll be satisfied with the working relationship. – Kimika Banfield, Arootah
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6. Ensure Your Assistant Is A Culture Fit
The most important factor when training a high-level assistant is culture fit. We look for motivated, high performers who are eager to learn. We encourage them to get to know the business by networking and meeting people. Knowing the key players will help them navigate any challenges they come across. – Leigh Yanocha, Knopman Marks Financial Training
7. Communicate Often
Make communication feel natural and easy, and do it often. Having someone manage your calendar or your correspondence is intimate so your communication frequency and style, while still professional, should match the level of closeness and transparency. You want them to be able to speak and act on your behalf, and the only way to do that is to let them in. – Ursula Mead, InHerSight
8. Invest In A Comprehensive Onboarding Process
The onboarding process will familiarize your assistant with your work style, preferences and priorities. Explain how you prefer to communicate, your decision-making process and any other personal or professional traits that will affect how you work together. Also, discuss limits of authority, which will help eliminate possible misunderstandings later. – Lisa Shuster, iHire
9. Be Fully Transparent
Share full transparency and guide them through your decisions; this will both enable higher commitment and generally much better outcomes, prioritization and execution. – Nick Frey, Avomind
10. Establish Clear Expectations And Give Feedback
A good start would be to establish clear expectations and foster open communication that can go a long way in creating a positive work environment. The next step would be to incrementally delegate with trust while providing constructive feedback. This is the type of work dynamic that takes time to build and requires both sides to be patient and eager to adapt. – William Stonehouse, Crawford Thomas Recruiting
11. Delegate On Day One
To succeed in the long term, a high-level assistant should be capable of working autonomously, foreseeing the needs of their supervisor and seeking support when needed. When supervisors give assistants the chance to accomplish tasks on their own, they instill confidence at an early stage and establish the tone for the rest of the relationship. – Niki Jorgensen, Insperity
12. Find An Assistant You Mesh Well With
Executives work closely with their assistants so it is imperative they work well together. Focusing on communication, culture fit, work style and flexibility are all important factors in determining how well the executive and assistant will work together. It’s important to ensure there is a personality match as well. – Erin ImHof, CertiK
13. Clearly Convey How You Operate
I am a high-energy, fast-moving and big-picture executive. I’m on calls or working on strategic projects from sunrise to sunset. Communication with me will be transactional. With that being said, It’s best for executives to be transparent in how they operate, communicate this and learn how their executive assistant operates to find a midpoint that meets everyone’s needs. – Nakisha Dixon, Vercara
14. Explain The Big Picture And How Their Work Matters
Your assistant is your business partner. Help them understand the bigger picture by sharing your strategic goals and vision. This allows them to understand how their work contributes to the larger objectives and is empowering and motivating. – Britton Bloch, Navy Federal
15. Hire Someone Who Requires Minimal Training
The best tip for training a high-level assistant is to identify and hire someone who requires minimal training. For this role, strong detail orientation and organizational skills are essential, and both can be evaluated during the application and interview process. By hiring the right person who possesses these skills, he or she will only need to learn your work style and personal preferences. – John Feldmann, Insperity
16. Create A Safe Environment
In addition to open communication and professional growth, create a safe environment where mistakes are seen as learning opportunities. Encourage authenticity; let them know it’s okay to not have all the answers. This fosters trust and encourages the assistant to grow into their role, promoting a durable working relationship. – Joseph Soares, IBPROM Corp.
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