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How to Get Through the Gatekeeper and Connect With Anyone

5 Insider Tips from the assistant to Robert Greene, a 6x NYT bestselling author 

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Image Credit: Unsplash

What is a gatekeeper in business?

Think of the bouncer at the door of an upscale restaurant, the muscle sorting out who to let in and who to keep out. Likewise, successful business professionals, politicians, authors and VIPs have someone that is in charge of protecting their time and space, letting in only a few based on certain criteria. You may not be aware of the power they wield, but it would be wise for entrepreneurs seeking contact to take heed of what it takes to get through the gatekeepers. 

Do your research first

Stop, look and listen. Your business could transform when you connect to the right people, so take the time to research your target connection before sending that email. What are their goals, struggles, and to whom have they already granted time? 

Prior to reaching out, spend time on their social media reading current and past content. Review everything on their website and listen to their interviews. 

5 insider tips from a high-profile assistant

1. What not to do

Do not approach with entitlement! While Stanley Goldberg, Robert Greene’s assistant (6x NYT bestselling author with his most recent being The Daily Laws), tries to give people the benefit of the doubt, some requests come in aggressively and cross the line. For example, complaining about the speed of an email response. No one wants to put a person like that through! Persistence is appreciated, but there is a difference between persistence and being demanding, and it’s usually those without big platforms that can be belligerent. If you approach with respect, an assistant will usually respond graciously as they know they are acting by proxy; it’s their boss’s reputation on the line. 

2. Recognize the privilege

An assistant is very careful with their boss’s time. As insiders, they witness the day-to-day diligence of how their boss takes their craft and business seriously. Scheduling, coordinating podcast interviews and appearances, managing social media platforms, and working on getting their boss’s name and business out to as many people as possible is usually part of their job. 

Goldberg is strongly aligned with Greene’s mission of teaching power, mastery, and psychological topics on human nature to the masses and believes that all people can benefit from at least one of Greene’s books. Working with the hope of somehow touching someone’s emotions so that they are prompted to buy one of the books is a very gratifying and privileged part of the job.

If you are a huge fan, say so! Detail what you got out of a VIP’s work, and be respectful in your communication, as that goes a long way in obtaining a possible connection. When asking for time, ask for a short time frame. It could be extended if you get a meeting and it goes well.

3. Provide value 

Who are you? Make sure that you include valuable accomplishments of your own in your email by way of links, a bio, and anything you have had success with, such as a podcast. Gatekeepers often go through it all, as they are looking to include whoever they can on their boss’s schedule. Additionally, many successful people like to pay it forward and help out a smaller podcaster and entrepreneur. While they can’t grant everyone an interview or personal interaction, they hope that people are respectful of that. 

4. Add a personal touch

Be vulnerable! Show that you genuinely care about the person and their work. Your courage in taking a shot at connection is admired by the assistant that knows what it takes to reach out to someone who is more famous and accomplished, trying to get a piece of their time that will mostly benefit you to grow your audience or impact your business.

Additionally, your personal request may not initially seem like the usual interview or connection granted, however if it seems like an unusual and interesting conversation may develop, you could be put on the schedule.

5. Be patient

Many gatekeepers have a lot of respect for the person they are working for as they are up close and personal with them. They are calculated with their boss’s time, making their own work-related interactions concise. When an assistant replies to an email asking you to contact them again in a few months, most do not – so keep trying.

Be confident and go for it. Goldberg says he himself got the job by a stroke of luck. While he had a love of publishing and marketing he was working as a soccer coach in NYC for kids trying to figure out his own direction when he answered a Tweet put out by Daily Stoic, and landed the job coveted by many.

In conclusion

Some additional tips: Use social engagement as well as your own network to get a referral and make a connection that way. Maybe someone you know could connect you. As far as who will benefit from the connection, think about how it will benefit them as well. 

Can you solve a problem for them? Value the gatekeeper, their perspective, and their job. They could end up putting you and your company in a strategic place on the map you could have never otherwise reached.

Esther Fink is an award-winning copywriter with awards from Oprah Magazine, Proctor & Gamble and others. She has a Masters in Organizational Psychology and combines psychology and writing to go viral.

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Success Advice

What Every New CEO Must Do in Their First 100 Days (or Risk Failure)

Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

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leadership tips for new CEO
Image Credit: Midjourney

When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
Image Credit: Midjourney

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

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Building a Business Empire: Lessons from the World’s Boldest Entrepreneurs

Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.

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