You have a new boss who is difficult to work with. How can you win them over?

If you work in trade shows, you know how important it is to have a good relationship with your boss. They can make or break your success, your career, and your happiness. But what if you have a new boss who is difficult to work with? Maybe they are micromanaging, demanding, or disrespectful. How can you win them over and make the best of the situation?

1 Understand their perspective

The first step to winning over a difficult boss is to understand where they are coming from. What are their goals, challenges, and expectations? What are their strengths and weaknesses? How do they communicate and make decisions? Try to see things from their point of view and empathize with their situation. This will help you to avoid taking things personally and to find common ground.

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Aun Raza

Engineering Manager | Generative AI | Software Developer | AI/LLM Product Innovator | Driving Innovation and Efficiency with AI 🚀🤖
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To win over a difficult boss, try to understand their perspective, communicate openly, maintain professionalism, set boundaries, and work collaboratively towards common goals.

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vince foster

Sales Specialist @ Sir Speedy PRINT/SIGNS/MARKETING - Music City | Print, Signage, Marketing
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When you receive the message that you have a new boss, we freak! Questions in our mind is , he or she going to like me, trust me or they will change everything I have been doing. RELAX! This will be fun and a new eye opener! Get excited about their views and input. Yes it's stressful but nothing you can do but embarrass them with open arms and except change.

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Marcello Flammia

Director - Security Advisory at mcrIT | Enterprise Cybersecurity Expert | Strategic Management | Operational Leadership Driving Innovation
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To win over a challenging boss, it's essential to empathise and understand their perspective. By comprehending their goals, challenges, and communication style, I would adapt my approach, find common ground, and build a positive working relationship based on mutual respect and understanding.

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Sarina Stokes

Founder and CEO "we are big friendly graphics!! " BFG Print limited Eco and sustainable print expert
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The boss may seem challenging because they have a hard task ahead and are keen to impress maybe the boss above them. running a business is not an easy task, so much to understand that you dont get to see as an employee..its essential to try to understand what this person is trying to achieve.. maybe ask them about their goals and remember to do your own job as well s possible,, its all linked

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Arun Nair

CMO | Marketing Alchemist | Crafting Futures | AI & Digital Visionary | Employer Branding Maven | CSR Advocate | Strategist with Heart | Empowering Brands & People | Inspiring Teams | Event Maestro
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Understand their priorities Communicate effectively Be proactive Seek feedback Build rapport Demonstrate reliability Adapt to their style Stay professional Show enthusiasm

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2 Communicate effectively

The second step to winning over a difficult boss is to communicate effectively with them. This means being clear, concise, and respectful in your messages. It also means listening actively, asking questions, and giving feedback. You want to show your boss that you are reliable, competent, and professional. You also want to avoid misunderstandings, conflicts, and surprises. Communicate regularly and proactively, especially before, during, and after trade shows.

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Marlène Liontis- Commercial Finance Broker-Liberty Adviser

Commercially Accredited Finance Broker @ Liberty Network Services P/L | SMSF Loans| Business Loans| Commercial Finance| Investment & Car Loans| Asset Finance| Debt Consolidation| Personal Loans & Residential Mortgages
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It is absolutely essential that strong boundaries are maintained and respected. Try to avoid "overfeeding" a negativity bias and instead, evaluate your interactions with them. Can you reduce your interactions with them? Can you try and practice detachment? Perhaps try and model the behaviour you want reciprocated.

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3 Deliver results

The third step to winning over a difficult boss is to deliver results that meet or exceed their expectations. This means doing your job well, meeting deadlines, and solving problems. It also means being flexible, adaptable, and creative. You want to show your boss that you are a valuable asset to the team and the company. You also want to demonstrate your initiative, enthusiasm, and growth. Deliver results that showcase your skills, knowledge, and experience.

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John McArthur

Managing Partner @ PAG CANADA, Ltd. | Award-Winning Sales Professional
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Try to understand their expectations, preferences, and goals. Building a positive relationship with a difficult boss requires patience, understanding, and proactive communication. Show initiative, deliver results, and seek feedback regularly. Demonstrate your commitment to the team's success and be open to constructive criticism. Building trust takes time, so stay professional, stay positive, and focus on building a productive working relationship.

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Kerry Diehl CIP CAIB

General Insurance Consultant | Producer | @InsuranceKerry
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Perform. Most bosses are looking to come down on something or somebody. Perform, and they will find a other target. Especially perform in areas that you know the boss's boss is watching.

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4 Seek feedback

The fourth step to winning over a difficult boss is to seek feedback from them. This means asking for their opinion, advice, and guidance. It also means accepting their criticism, praise, and suggestions. You want to show your boss that you are open to learning, improving, and developing. You also want to align your goals, priorities, and strategies with theirs. Seek feedback that helps you to understand your performance, your progress, and your potential.

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5 Build rapport

The fifth step to winning over a difficult boss is to build rapport with them. This means finding common interests, values, and hobbies. It also means showing appreciation, gratitude, and respect. You want to show your boss that you are a human being, not just an employee. You also want to create a positive, trusting, and friendly relationship. Build rapport that makes your boss feel comfortable, supported, and appreciated.

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6 Set boundaries

The sixth and final step to winning over a difficult boss is to set boundaries with them. This means being assertive, respectful, and honest about your needs, preferences, and limits. It also means saying no, negotiating, and compromising when necessary. You want to show your boss that you are confident, independent, and responsible. You also want to protect your health, happiness, and sanity. Set boundaries that balance your work and your life.

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7 Here’s what else to consider

This is a space to share examples, stories, or insights that don’t fit into any of the previous sections. What else would you like to add?

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You have a new boss who is difficult to work with. How can you win them over?

1

2

3

4

5

6

7

1 Understand their perspective

2 Communicate effectively

3 Deliver results

4 Seek feedback

5 Build rapport

6 Set boundaries

7 Here’s what else to consider

Trade Shows

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You have a new boss who is difficult to work with. How can you win them over?

1

2

3

4

5

6

7

1 Understand their perspective

2 Communicate effectively

3 Deliver results

4 Seek feedback

5 Build rapport

6 Set boundaries

7 Here’s what else to consider

Trade Shows

Rate this article

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