How to talk to your boss about the restrictions in your position and limitations that your boss is causing?

Talking to your boss about difficulties you're having working with her/him can be intimidating. But there are definitely ways to make it easier. I'll share with you a few general ideas, and then dig into your specific situation.

In general:

I can think of three approaches you might use to bring this up with your boss. They all basically achieve the same end goal: having a positive conversation that brings you to alignment with each other about what the expectations are for your role and how you can work together to achieve success.

1. The Consultation: "Hi <boss name>. I'm having some difficulty with how to approach fixing the video recorder bug. So far my approach has been to find new recorder options to bring in. I feel like perhaps that's not the approach you were hoping for. Could we sit together tomorrow briefly to discuss what your expectations are for the bug fix there, and discuss pros / cons of various approaches to resolving that bug?"
2. Ask for coaching: "Hi <boss name>. I'd like to ask for your feedback and coaching related to how I can better support you with fixing the video recorder bug. I feel like I've tried a few things, but that they are not quite what you are looking for. Would you be open to speaking with me tomorrow or the day after to provide me with a bit of coaching on what kind of solution you're hoping to get, and perhaps walk me through an example? I think that might help me to learn, which I can use to better collaborate with you on other tasks in the future."
3. Give feedback: "Hi <boss name>. Would you be open to meeting tomorrow so that I could provide a little bit of feedback on some of the great vs. harder things about our communications on our current project... and enter into a discussion with you to co-design how we can collaborate even more smoothly in the future?" (IMPORTANT: Not everyone takes equally well to receiving feedback from more junior team members. I personally love to get feedback from everyone, and I solicit it, but that's not the case for all. I'd use this option only if I were quite sure that the person I was offering feedback to was going to be thankful to receive it. And if you do choose to give feedback, the burden is on you to be very specific, and very clear, and ultimately very encouraging)

One thing you may have noticed is that in all three notes, I'm trying to get to an in-person meeting. That's because you will be much more likely to understand each other and avoid miscommunication if it's done live. If you cannot meet in person, at least try to set up a video call or phone call. As a general rule, I only try to resolve conflict in written form as an absolute last resort. It is much much less effective, and less likely to succeed if it is done in purely written form, in my experience.

Your specific situation:

it sounds like your boss is asking you to fix something, but doesn't want the type of solution you are providing. Are you offering new widgets, when s/he just likes the widget they have and wants that one fixed? If so, perhaps the disconnect is that s/he thinks the current widget is something you can fix, and you don't. Is that correct? Or am I missing something about this situation. If I'm understanding correctly, then you might also have an option to say something like "It sounds like you'd really like the current widget fixed, rather than replacing it. At the moment I don't know what's wrong with the current widget, or how long it might take to find the bug and fix it. I can find other widgets, but if you think it is very important to try to fix the current one, then could I ask roughly how much time you think I should invest in trying to fix the current one before we consider switching to a new one?"

Source: Personal experience, from resolving conflict, working with bosses, and being a boss.

Leah,

It's frustrating when you are given a job to do but not given the latitude to do it!

However, the one thing you do NOT want to do is tell him you can't do it!

Learning how to persuade others to your point of view is something you will need to do throughout your career.

It gets easier over time. But, when you are first starting out, you don't have a "proven success record" to stand on,

and it's not so easy. Also, some people are a bit more resistant to change. Sometimes there is no real reason for it.

Other times, there may be budgetary constraints.

Since you do not have the authority to do the trial runs, do the next best thing.

Find the on-line reviews from others, and write up a short report with your top 3 picks, summarizing the on-line reviews.

Talk to those who are using it, if possible. You could also address which ones you definitely think you should NOT go with, and why.

Include pricing information.

As to other changes on the website, keep in mind that he probably designed or approved the current layout.

Now you want to tell him that it could be better. ouch! Unfortunately, some people take this personally, and their feelings get hurt.

Be careful about being critical of it. You could approach it in a more neutral way.

Perhaps pointing out that the changes you want to make would make it easier for people with disabilities to navigate (that would be cool!),

or that trends/styles have changed over time and that while the current layout was cutting edge at one time,

the changes you want to make would keep it current. But again, be able to back up what you are saying.

What you want to do is establish credibility. Once you do that, and he knows that you know what you are talking about,

you will have more latitude with your work! It's a slow process.

Also, the source of your frustration is this: Basically, you have been delegated an assignment, but not given the authority to do it. I can't find the quote, but, I etched it in my mind the first time I heard it: Responsibility, Authority, And Accountability are like a 3-legged stool - all three go together.

One final word of advice: try to avoid the trigger words when talking to him. Always, never, can't, won't etc. Keep it positive!