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Tips for Better Conversations in Your Career and Business

Updated: May 5, 2021


Conversations in the workplace often come down to pressing send, or submit on an email or other app. We’re often so busy in our career or business that it’s easier to communicate with a quick response from our computer or phone so we can get back to our tasks than to take the time to have a real conversation.


You meet a multitude of different people throughout the day. How often do you take the time to have a face-to-face conversation with any of those people to learn something about them? If you’re like most people, you have a lot on your plate and you feel that you just don’t have enough time to complete your tasks and give people the more personal or one-on-one time they deserve.


Has it been so long ago that you forgot what it’s like to have a meaningful conversation in your career or your business? When you talk to others, is it to just say “Hi, it’s nice to meet you,” or “Thank you,” when you make a sale?


Typically. there are three goals or purposes of any conversation. They include:


· Goal #1 is simply to have the enjoyment and pleasure of expressing yourself and interacting with others. Humans crave interaction with others who have the same likes or who are associated with a something we find exciting and inspiring.


· Goal #2 is to get to know others better. In business, it’s necessary to talk with others to learn how they are likely to feel and think about a variety of subjects, as well as predict how they will react to what you say and offer. This won’t happen overnight. Customers often need to talk with you several times before they trust you enough to get involved with your business. That is why having timely conversations to get to know other people is critical to your success and their satisfaction.


· Goal #3 is to build trust and likeability between you and the other person. This is important not only in business but in every aspect of your life. Initiating and participating in meaningful, informative, empathetic conversations is often how you build trusting relationships.


Building your skills to have better conversations in your career or business helps you reach your goals and build relationships with others. Throughout this guide you’ll find why conversations help you reach your goals along with samples of conversations you can implement in different situations.



Why Better Conversations Help You Reach Goals. Hint: It's About Time and Trust.


Whatever kind of relationship you are building, the foundations will be built on the ability to trust each other. Human beings generally afford each other a measure of trust initially. From there forward, it is all about building or destroying that trust. Trust is developed by communication and consistency. For example, if I tell you I am going to do something and then I actually do it, I build trust with you. If I don't do it, barring an exceptional circumstance, I lose trust with you. If I am inconsistent enough times, you will never really trust me again. It's human nature. It is important to know how to build and maintain trust for a successful business relationship.


How can having better conversations help you reach your business or career goals? Believe it or not satisfied customers are ones who you have built a relationship with. The conversations that take place in your business or where you work between your customers and you, your employees or among you and your employees, are key to reaching strategic goals.


It’s important to communicate effectively in both the external parts and the internal areas of your business. Invest time money and resources creating good customer care when dealing with customers. But at the same time, invest the time to build relationships with those who you work with daily. This helps build relationships that help you grow not only as a business but as a person as well.


Having better conversations helps boost employee engagement, increase productivity, and builds better team cohesiveness. In your career it helps you build connections and relationships with others who can help you advance, build friendships and lasting associations. The magic key to enhancing trust is compassion; not the kind where you are simply kind, but where you actually care. The best two gifts you can give to another human being are understanding and appreciation.


Boost employee engagement by having deeper conversations with them. Get to know them by asking what they need, helping them with any interpersonal problems when possible, and talking to them as individuals not just employees. Let them know what you expect from them and how their work contributes to the bigger goals of the company.


Increase productivity by creating teams which communicate well with each other. When you have employees, who miss or are late for work frequently, show your concern about them by finding out the underlying problem and helping them to brainstorm solutions. Ask if there is anything you can help them. Be open and listen to your employees, coworkers, and customers to decrease problems and increase productivity.


Foster teamwork by getting to know each team member’s skills, strong points, weaker areas, likes, dislikes, preferences, and comfort levels in a variety of situations. The more you learn about each team member, through in-depth conversations, the more you understand what each person needs to work at optimum efficiency and identify the type of people with whom they work best.


Participate in comprehensive conversations to help you understand the expectations others have of you. These conversations help you build relationships with coworkers, your boss, and others, with whom you come in contact. When these people get to know you and your excellent work, they can help promote you in your career.


Being able to have good conversations helps you connect with others, learn new things and share ideas that can help you succeed. Conversations are how we deepen relationships, solidify, or grow our reputation and avoid conflicts.


Creating and having better conversations are an important part of your career or business as the day to day operations are about people.


Have Better Conversations at Work


Now that you know why having better conversations can help you be successful in your career or business, it’s time to learn how to make worthwhile conversations. Here are few tips to get you started:


· When you are in a situation at work that is frustrating, begin by thinking about what you’re feeling or thinking about. When you have an unwelcome emotion at work, such as frustration, anger, or disappointment, examine that feeling instead of ignoring it. What caused it? What’s the reason behind it? How is your mindset affecting your actions?


· Before talking to anyone about the situation, write down what you want to say. In advance, plan out the points you want to highlight. Begin with your appreciation. Mention your concern for the person, due to a specific change in behavior or attitude.


· Be open and listen before you speak. Active listening requires actual attention. Don’t formulate an answer in your head before you hear what the other person has to say. If you are thinking of the next thing to say, you aren't really listening. Repeat or rephrase what the person has said to confirm it or clarify what you heard. This works in three ways. First, it makes the other person feel heard. Second, it clarifies points of misunderstanding. Three, it builds trust and compassion between the participants.


· Ask questions when people finish speaking. If you need more clarification, wait for a lull or break in the conversation to bring your question to the person’s attention.


· Choose the right words for the conversation, the person and the situation. Don’t use foul language in a business situation.


· Make sure your body language matches your words. If you stand with your arms crossed but say, smiling, that you are open to what they have to say you are sending a mixed message to others.


· Don’t talk excessively, controlling the conversation. Good conversations need balance where each person understands and is understood. Be aware of how much of the conversation time you are taking. Finish your point and then counter with an open-ended question.


· Leave technology on the desk. Whenever possible have a conversation in person. Don’t rely so much on technology to communicate your message. The subtleties of body language, tone and disguised meanings are all lost with the convenience of pushing a button. There will be less chance of lost translations when you talk to someone in person.


Work conversations tend to be less personal but still need to adhere to standard conversation guidelines. Listen carefully. Ask open-ended questions. Use the correct words and phrasing. Engage with the other people and share your observations and ideas regarding the topic of conversation.


Tips for Different Situations


Different situations call for you to engage in different conversation types. It doesn’t matter whether you’re an introvert, extrovert or somewhere in between, sometimes the conversations are easy. However, there will be times and conversations, in which you have difficulties understanding what is being said or making yourself understood.


Overthinking won’t help but neither will not having a plan of action or a backup repertoire of topics you can fall back on regardless of who you’re talking to. When you fumble for what to say, avoid impromptu conversations or always go back to talking about the weather, follow the below guidelines to help you in any situation you might find yourself in your career or business.

1. Talking to Founder or CEO Communication


Be the initiator. Start the conversation by asking them a question. Give them a chance to share information with you by asking an open-ended question. It can lead them into talking excitedly. Be prepared to listen intently, and ask thoughtful questions when they are finished.

It can also result in the CEO politely asking you how your work week is going. In this case be ready to have a straightforward but intelligent answer. Talk about something you are working on and for what department you’re in.


Big organizations the owner or founder may not remember what your role is in the company. It’s fine to give them any relevant information that will help them place you. And be sure to introduce yourself (again) if you don’t think he knows your name.



2. Talking to a New Person


Start the conversation by introducing yourself and asking them about themselves and if they’re getting settled into the new company. It’s not easy being the new kid so help put them at ease. Make a point to appreciate the growth of the company and the culture of new people. Don’t wait for your colleagues to shoulder the responsibility of learning more about the newbie and befriending them.


3. Talking to an Intimidating Colleague Communication


Instigate the conversation by asking them a question about something in their expertise, for example, suggestions for places to network during lunch. You could ask about a work-related topic if you know what they do or what they’re working on.


4. Talking to an Event Organizer

Compliment the person about the event or space, thanking them for organizing it. The ask something about them, such as “Do you plan things like this often?” Most people enjoy talking about themselves. Use it to your advantage. This is especially handy if you have no idea what to say to that person you’ve just met.


5. Talking to a VIP


Introduce yourself and compliment them about their product, program, book or whatever they are known for. Compliments often incite discussions so go ahead and compliment, just be genuine in your praise.


6. Talking to a Previous Boss


No matter the terms of your departure, don’t pretend like you didn’t see them. Approach them with a pleasant greeting. Talk about the company/department you worked for and ask open-ended questions about their role in the company’s expansion, project, product, etc.


7. Talking to a Department Co-worker


You can open with a vague question such as “How’s your week going?”. This lets you off the hook about not knowing exactly what they do (and they most likely aren’t familiar with your daily work either). Make an effort to engage them in a conversation by asking about his job or department. If he’s not forthcoming about what he does and the projects his team is working on, you can always start talking about something your department is working on.


8. Talking to a New Intern


Initiate the conversation by asking them about what they’re watching or reading right now. When you start the dialogue about entertainment subjects like TV, books or movies you won’t struggle to find things to discuss. Unless they are totally off the grid, you’ll find at least one thing you share interest in. It might even be something you disagree about.

9. Talking to a Boss’ Partner or Spouse

Start the conversation with a compliment and talk about something your boss mentioned about them such as she likes to cook with her significant other. If you can’t remember something your boss has said, then ask what she does.

Beat Fear with Conversation Tips


These are all partially pure speculation so it’s up to you to improvise. But these tips will give you the initiative to approach and start conversations that might be intimidating. Be yourself, be sincere and know that conversations take some type of effort by most people. So far, you’ve learned why conversations can help you succeed and how to initiate conversations in different types of situations. If you’re still afraid and filled with anxiety when it comes to having a conversation, this section has you covered.

Most people are fine when they feel confident and comfortable. They can easily converse with others. But when they have social anxiety disorder, or are nervous and afraid, which happens all too often in business and work situations, it’s another story. The good news is you can learn different ways to start conversations that are effective. The key is to practice so you get better.


Begin by keeping it simple. Have a follow up plan after the initial hello, how are you. Don’t use a clever ice breaker that could blow up on you. Leave the jokes or snappy stories out of the initial conversation as well. Too risky! If they land wrong, there goes your favorable first impression.

Be yourself and don’t try to say something that isn’t natural to your personality. Give them a compliment about something such as a project they just finished, a presentation they gave or how organized they are.


Ask open-ended questions that require more than a yes, no, time or date. Ask something that invites a response that will draw the other person out, giving you the opportunity to listen and respond accordingly.


The topic for the first question should be rather generic, especially if you don’t know the other person well. Here are some ideas:


· What do you think of the food for this event?

· Parking was difficult for me. How’d did you get here?

· What do you think of the theme for this event?

· I’m new to this company and the area. What are the best places to grab lunch?


Stay away from controversial topics until you know the other person better. It’s a good idea to stick to the weather or other non-political events such as sports or news events or something related to your industry as conversation starters in the workplace. Ask what you colleague thinks of the latest acquisition or the new sales figures, for example.


Practice nonverbal communication techniques. Make yourself more approachable by using different body positions and gestures that communicate to other. This includes nodding when others are talking, maintaining eye contact or simply mirroring the speaker. Smile, lean in slightly but be aware of personal space, avoid crossing your arms or legs, and make eye contact with the other person.


Get the other person talking about themselves. Ask the right kind of questions to encourage the other person to open up. This gives you time to listen and get more comfortable around them. Ask about their hobbies, a favorite food or holiday or their family.


I know I said be yourself, but doing your homework is a way to increase your confidence and give you talking points. If you are attending an event or meeting, ask for a list of guests ahead of time. Then you can use sites like LinkedIn to find out about them. This gives you the perfect background information for a conversation opener.


Practice makes you feel less anxious and helps you get better at having conversations. Find ways to strike up conversations with other regularly, such as talking to the person in front of you at the grocery story line. Say good morning and ask a follow-up question to the older guy you see every day at the park. These safe scenarios help build your confidence, making it easier to transfer those skills into the various business or social settings you come into.


Finally, don’t let a conversation mishap or failure throw you. Not every conversation is going to be easy. As you strive to gain confidence and have more conversations, you’ll most likely encounter people who will reject your efforts and not be interested in talking. Some might be rude to you. Don’t take this to heart. They may be having a bad day, be shy or have something distracting on their mind. Simply smile and move on.


If you flub up, stutter or make a mistake about a subject, laugh it off, make a joke about it or simply ignore it and move on.


Your ability to carry on conversations at work and throughout your career is invaluable to your success. Getting past your fears and anxieties takes practice and a bit of initiative but will serve you well in the end.


Difficult Conversation Tips


There will be times in your career that you might have to have a difficult conversation with someone you work with or for. We often have a fear of conversing about a sensitive subject. That fear is sometimes worse than the conversation itself, making us put off brining up a tough subject. We’re waiting for the perfect opportunity or the right time. But there is usually not perfect time.

That’s why nearly seventy percent of employees avoid difficult conversations at work, according to a study by career-coaching group Bravely. (source: https://learn.workbravely.com/cost-of-the-conversation-gap) Here are 7 tips to help you have that conversation.


1. Don’t avoid it and go to the Source. The longer you wait the harder it will be to have the conversation. If you have to have a conversation that is intimidating you, set up a time to chat with the other person, stating it’s about something delicate. This lets them know that you need their attention and it’s possibly going to be a tough conversation. Also, don't talk to other people before you speak to person who is the source of the conversation. This limits the possibility for misunderstandings and erosion of trust not only with that person, but others in your work environment.


2. Know why you are having the conversation. What’s your purpose? Write down two to three things you want to accomplish and focus solely on them. Stick to the facts that you know to be true. And take responsibility for your part in the situation.


3. Be confident or at least pretend to feel confident. Take the initiative and begin with confidence, getting to you point quickly. If you feel anxiety, breathe slowly. Far too often people don't utilize silent pauses that present themselves in a conversation. In difficult conversations, these silent moments can be very useful as a time to gather your thoughts, put emphasis on a point that was made, or as points of reflection or correction.


4. Be open to the other person’s point of view. Most meaningful discussions have multiple perspectives, ideas, or solutions regarding a topic or issue. The exchange of information and options or possibilities may open up new doors to resolution.


5. Start each sentence with “I” or “We” instead of “you”. This avoids putting the other person down or on the defensive. “I” statements promote positive communication channels and help foster enthusiasm so you can find a solution. The “I” statements make a huge difference between constructive and critical feedback. Use “we” when you want to convey the idea you are willing to help.


6. Come up with a solution by working together on a course of action you agree upon. Listen to the other person’s ideas as well as offer your own ideas.


7. Follow up to prevent any fallout later. Some people may have a delayed reaction to bad news and feel embarrassment after leaving the conversation. Check on the other person occasionally to make sure they are doing alright.


Everyone’s had a difficult conversation related to their job or career. The trick is to refrain from avoiding the inevitable. Address issues head-on in a diplomatic and caring way. The more quickly you address and solve a problem, the more effective the results are.


Do This Next


Your career or business depends on how well you can communicate with others. Learning how to have better conversations that help you build relationships and get to know those who you serve and work with is key to success.


Determine what type of conversation you want or need to have before you jump in talking. You don’t want to come off as overbearing or getting too personal. On the other hand, you don’t want to come off as standoffish either.


As an introvert or someone who suffers from social anxiety disorder, meeting new people and having a conversation with them can cause real fear. Learn specific tricks like having topics or questions you can fall back on if you don’t know what to say. And practice regularly initiating conversations with people you meet at the grocery store, the gym or in your daily life.


Finally, don’t put off having difficult conversations at work. Be diplomatic and empathetic. Talk with the person to understand the situation better, before diving in about the issue. Be confident, yet kind while addressing an issue. Make use of silent pauses. Listen with an open mind to find a variety of solutions. Follow up to recap after the meeting.


Having better conversations in your business is necessary in every area, from product development and marketing to customer support and sales. Practice honing your communication skills by embracing and participating in conversations that go beyond the “social niceties” of “Hi, how are you,” to make it more meaningful to all involved. Build the trust and respect you want to have through good communication. Good luck and have fun!

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