Why Do We Struggle with Negotiations? | Negotiation Part 1
Your client just called with an "urgent" change request that renders the work that your team has done so far abortive, and they have to rework on the design again. Your mind races between:
"How are we going to pull this off?"
"If I push back, will they think I'm difficult to work with?"
Negotiations are something I struggled with many times. I felt intimidated, unconfident, uncomfortable even before I started speaking with the other party. Whether it was negotiating for a change in deadline, scope of work, design fees, or even at home, trying to get my child to spend less time on devices, games...
When I was starting out, I had a foolproof strategy: escalate to the boss. Why deal with the discomfort when I could delegate this difficult task away? But when I stepped into a leadership role, I am the boss now, escalation is no longer an option.
I still remember my first official negotiation conversation. My boss was kind enough to offer help and join me in the meeting. My mind was desperate for that safety net. Back then, I thought my only job was to convince the other person to say yes to my proposal. I was so nervous that I may fail, that I may fold too quickly and accept whatever they offered instead. But I knew I had to sit with that discomfort and try, otherwise I would never learn. So I said no to his offer. I prepared the responses for all the possible scenarios or counter offers that could come my way. I walked into that meeting room alone, anxious but ready.
That meeting helped me develop more confidence in negotiations, it wasn't as daunting as I expected. What it taught me is that practice matters, and it’s always best to start with a low-stakes situations. Your first attempt may not go perfectly, and that’s okay.
Preparation is key, and that’s why I’m writing this 2-part series: Part 1 explains why we struggle, and Part 2 will share techniques I’ve used, inspired by two negotiation books.
What Makes Negotiation So Uncomfortable
Wanting to be the 'good employee'
Most workplace negotiations feel challenging because we’re negotiating relationships. We’re talking to people we are working closely with, people whose approval affects our career trajectory, people whose recommendations can make or break future opportunities.
We rather say yes to unreasonable requests than risk being seen as difficult, uncooperative, or not a team player.
A common scenario: when a project manager came to you with an “urgent” task. You knew you had other project deadlines clashing, but said yes anyway. You didn’t share your other commitments, didn’t negotiate a realistic timeline. You just agreed, stayed silent, and pushed through until 2am. To the PM, it probably seemed like you could handle it easily. But you suffered in silence, feeling frustrated and unseen.
Boundaries actually make you more valuable. When you consistently deliver quality work within realistic parameters, you become the person others can truly count on, not the person who overpromises and underdelivers.
Power imbalance
The challenge of perceived power imbalances. When you’re negotiating with your boss, a key client or a senior stakeholder, it is natural to feel like you’re in a weaker position.
Another scenario: your client requests endless design revisions, each one chipping away at your timeline and budget. You know it’s out of scope but you fear pushing back may damage the relationship. So you say “okay,” and swallow the discomfort, then you and your team pay for it later, burning out quietly. You feel like you have no room to push back because of the hierarchy.
Not knowing what to ask
There is the fear of not knowing what’s reasonable to ask for. Should you push for a 2 weeks extension or is 1 week more realistic? Is asking for additional information going to make you look out of touch? Without clear benchmarks, we often default to accepting whatever is offered rather than risk appearing unreasonable.
I come across this often, where we underestimate the true effort needed to complete a task. We over-promise, under-deliver or push ourselves trying to meet unrealistic deadlines we never challenged in the first place.
The Negotiation Mindset Shift
The mindset shift came when I stopped thinking about negotiations as arguments to win and started seeing them as opportunities to understand the other side better and achieve a win-win situation. As Chris Voss mentions in Never Split the Difference, tactical empathy is the key to negotiation.
Very often in an argument, how many times did proving someone wrong result in them saying, “Thank you for telling me that. I was wrong. Now I see the light”? Not so often.
Instead of convincing the other party they’re wrong, we should be open to understand their perspective, challenges, difficulties. Show that you care about helping them achieve what they need while establishing your own requirements.
When I started applying tactical empathy not only in formal negotiations but in everyday conversations with colleagues and clients, everything shifted. I began to see negotiations as collaborative problem solving sessions where everyone could win.
Why Do We Feel Anxious?
Feeling anxious is normal. It is your brain doing exactly what it’s designed to do, to protect you from perceived threats to your social standing and security.
When you understand that your discomfort is normal and predictable, you can start to work with it instead of being paralysed by it. You can prepare for the physiological response and have strategies ready to manage it.
The most successful negotiators aren’t fearless, they’re just better prepared and more skilled at managing their fear.
Final Thoughts
Every negotiation is an opportunity, to reach an agreement and connect with the other person. To really understand what they need, and to find a way for everyone to succeed/win.
Negotiation is a skill that requires practice to win at negotiations.