Guest Speaker Series – Gabriela Bojilova – Difficult Conversations

Nov 19, 2021

“Sales teaches you the right skills to have conversations. Life skills and professional skills align and the skillset learnt can be used in both.” 


Gabriela Bojilova started out her career teaching English in Spain, where she developed her relationship-building skills. She then went on to work for recruitment company Phaidon, where she learnt how to sell, before joining cyber security firm, Tessian. At Tessian Gabriela worked with SaaSLeads Co-Founder & COO, Chris Ritson and had a solid run as an SDR. From SDR she was promoted to Account Manager, where she worked directly with customers to understand their needs and pains. Gabriela joined us at the Academy to discuss difficult conversations and why it’s important to learn how to navigate them.


Why are difficult conversations difficult?

Difficult conversations are usually tricky because you’ve thought of the possible outcomes and negative consequences of that conversation. There’s a risk or perceived risk, but it’s usually not as dangerous as we think and often the anticipation is worse than the conversation itself.

When there is emotional uncertainty of how the person is going to perceive the conversation it can affect our confidence and result in repeatedly reciting the conversation. 


Why are difficult conversations important?

Though it seems easier to not have that difficult conversation in the long run it is usually better to, in order to gauge how the other person is feeling about the situation and whether it aligns with how you feel too. It is possible your opinions already align and you can move forward, or on the other hand, you deal with any challenge faced and realign. 

Having difficult conversations is also important to build trust between the two parties involved. 


Gabriela’s three methods for nailing that difficult conversation 

1. The Sandwich method

The first method Gabriela discussed was the sandwich method. The hack is to sandwich the negative feedback in between positive feedback:

  1. First, provide positive feedback or a compliment. 
  2. Then offer the negative feedback with coaching on how it can be rectified. 
  3. Finally, give more positive feedback and encouragement. 


Why this method is effective from SaaSLeads Team Lead Sonia Gonzalez Guillonneau

The negative feedback is double the value compared to the positive feedback in the human brain, so when you sandwich it with positive feedback the positive feedback increases in value. 


 2. Velvet hammer

The velvet hammer is soft like velvet but packs a punch.  

It includes using phrases like: 

  • “I noticed”
  • “I was wondering” 
  • “What’s the likelihood”

For example:

I noticed you’re running behind on your deadlines and I was wondering what you think we should do.” 

Frame the conversion as a team effort – use ‘we’ because it means you share the responsibility and it’s not put solely on the person receiving the feedback. 

Follow up with an action phrase like:

What’s the likelihood you will be more on track with the project.”

It is important to ask questions to understand rather than to blame. If you build a relationship with a person then you are usually able to have a more direct approach and you will know how that person likes to receive feedback. 


 3. Utilise resources

There are so many useful resources you can source that will help you nail that difficult conversation. Gabriela extracted a fear framework from the book Feel the fear and do it anyway by Susan Jeffers that she believes is compelling. 

There are three stages of fear: 

Level 1 – things that happen or require action.

Level 2 – the risk of rejection, which is often made worse through negative inner dialogue.

Level 3 – the fear that you can’t handle it. At the base of every one of your fears is simply the fear that you can’t handle whatever life may bring you.


Changing your perspective

Instead of fearing and dreading conflict view it as an opportunity to learn, grow and understand. The only way to create change and grow is through challenging ourselves – it’s always a win-win situation. It either goes well or you have to grow and develop.


Gabriela’s how-to guide for difficult conversations in sales

In sales, we have difficult conversations every day. Here are three tips on managing them:

  • Ask good questions and intentionally listen to the answer instead of interpreting.
  • When you’re negotiating read body language and the room to understand the best phrasing to use. 
  • Control the controllables – you can’t control people’s emotions and reactions, but you can control your thoughts. 


Gabriela’s final words 

The best thing you can do is try and when you keep doing that you will win eventually. Remember that you can handle every conversation you deal with. Don’t let fear and anticipation keep you from growing. 

Get rid of the word difficult and just say conversation. 


Key Takeaways 

  • Difficult conversations are usually difficult due to a risk or perceived risk
  • Sandwich negative feedback in positive feedback
  • Don’t let fear drive your car – acknowledge it, but don’t let it control you
  • Keep going – keep trying
Lena Miah

Lena is our Marketing Executive here at She is versed in all things marketing and loves creating thought provoking, inspirational, and informative pieces for the company. 

Lena was born and raised in London. She has a passion for all things words and completed a BA degree in Journalism at the University of Roehampton. 

When she isn’t keeping the company blog in tip top condition she can be found in a yoga class or checking out the London food scene, but if the food isn’t up to par she could bake it all herself. 

You can find Lena on LinkedIn here 

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