The problem is that you have structured the Tkinter program incorrectly.
In "gui.py" you should have something like:
from Tkinter import *
gui= Tk()
gui.mainloop()
You can add buttons to perform functions and customize it:
from Tkinter import *
gui = Tk()
gui.title("This is a GUI")
def launch():
execfile("gui.py")
launchbutton = Button(gui, text='Launch Program', command=launch)
launchbutton.pack()
gui.mainloop()
I think with your function buttonWin
you were trying to do what is normally handled by a class; see unutbu's answer here.
I'm not sure if I've addressed your problem, but this should be a start.